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(4R,6S)-tetrahydro-4-hydroxy-6-phenyl-2H-pyran-2one | 148495-64-1

中文名称
——
中文别名
——
英文名称
(4R,6S)-tetrahydro-4-hydroxy-6-phenyl-2H-pyran-2one
英文别名
(4R,6S)-4-hydroxy-6-phenyloxan-2-one
(4R,6S)-tetrahydro-4-hydroxy-6-phenyl-2H-pyran-2one化学式
CAS
148495-64-1
化学式
C11H12O3
mdl
——
分子量
192.214
InChiKey
YLSYWCHDUMVJIL-ZJUUUORDSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    397.4±42.0 °C(Predicted)
  • 密度:
    1.238±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    1.1
  • 重原子数:
    14
  • 可旋转键数:
    1
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.36
  • 拓扑面积:
    46.5
  • 氢给体数:
    1
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

点击查看最新优质反应信息

文献信息

  • A Concise Total Synthesis of Diospongins A and B
    作者:Gowravaram Sabitha、Pannala Padmaja、Jhillu S. Yadav
    DOI:10.1002/hlca.200890242
    日期:2008.12
    The total synthesis of the diarylheptanoids (−)-diospongin A (1) and B (2) was achieved stereoselectively via the δ-lactone intermediate 6. The key reactions involved are a stereoselective reduction of β-keto ester and the Horner–Wadsworth–Emmons and intramolecular oxy-Michael reactions.
    所述二芳基庚的全合成( - ) - diospongin A(1)和B(2)中的立体选择性地实现经由所述δ -内酯中间体6。涉及的关键反应是β-酮酯的立体选择性还原和霍纳-沃兹沃思-埃蒙斯分子内和分子内的氧-迈克尔反应。
  • Studies on the stereoselective selenolactonization, hydroxy and methoxy selenenylation of α- and β-hydroxy acids and esters. Synthesis of δ- and γ-lactones
    作者:Carmela Aprile、Michelangelo Gruttadauria、Maria E Amato、Francesca D'Anna、Paolo Lo Meo、Serena Riela、Renato Noto
    DOI:10.1016/s0040-4020(03)00206-0
    日期:2003.3
    The diastereoselective synthesis of hydroxy substituted γ- and δ-lactones was accomplished following two approaches. A 5- or 6-endo cyclization promoted by electrophilic selenium reagents of α- or β-hydroxy acids and a 5- or 6-exo cyclization of hydroxy esters obtained through a diastereoselective hydroxy selenenylation reaction of α- or β-hydroxy esters. Moreover, the diastereoselective methoxy selenenylation
    羟基取代的γ-和δ-内酯的非对映选择性合成是通过两种方法完成的。的5-或6-内环化促进由α-或β羟基酸电硒试剂和一个5-或6-外通过α-或β-羟基酯的非对映选择性羟基硒烯化反应获得的羟基酯的环化。另外,对上述化合物的非对映选择性的甲氧基亚硒基化进行了研究,结果表明在羟基亚硒基化条件下不反应的化合物在甲氧基亚硒基化条件下产生了脱保护的二醇。通过制备不对称官能化的对称化合物证明了甲氧基亚硒基化方法的有用性。发现产率和选择性取决于取代基(经历亲核攻击的碳原子上的Ph或烷基),环化方式,动力学或热力学控制条件。在后一种情况下,硅胶起着重要作用。
  • In search of open-chain 1,3-stereocontrol
    作者:Asun Barbero、David C. Blakemore、Ian Fleming、Robert N. Wesley
    DOI:10.1039/a607545b
    日期:——
    Methylation of methyl 4-phenylpentanoate 25 gives the diastereoisomers methyl (2RS,4SR )-2-methyl-4-phenylpentanoate 26 and methyl (2RS,4RS)- 2-methyl-4-phenylpentanoate 27 in a ratio of 44∶56. The aldehydes 3-dimethyl(phenyl)silylbutanal 28, 3-dimethyl(phenyl)silyl-3-phenylpropanal 32 and 3-dimethyl(phenyl)silyl-4-methylpentanal 36, each of which has a stereogenic centre on C-3 carrying a silyl group and successively also a methyl, a phenyl and an isopropyl group, react with a range of methyl, phenyl and isopropyl nucleophiles to give pairs of diastereoisomeric secondary alcohols 40–42, 47–49 and 54–56 having 1,3 related stereocentres. The same alcohols 43–45, 50–52 and 57–59 are also prepared by reduction of the corresponding ketones 29–31, 33–35 and 37–39 with a range of hydride reagents, and three of the ketones, 31, 35 and 39, react with phenyllithium to give mixtures of the tertiary alcohols 46, 53 and 60. The (E)- and (Z)-α,β-unsaturated methyl esters, 61, 62, 64, 65, 67 and 68, prepared from the same three aldehydes with methoxycarbonylmethyltriphenylphosphorane, react with the phenyldimethylsilyl-cuprate and -zincate reagents to give diastereoisomeric pairs of 1,3-disilylated esters. Likewise, the α,β-unsaturated dimethyl diesters, 63, 66 and 69, prepared from the same three aldehydes with dimethyl malonate, react with phenyldimethylsilyllithium and the corresponding cuprate and zincate reagents to give diastereoisomeric pairs of 1,3-disilylated diesters, and with various methyl and phenyl nucleophiles to give the corresponding pairs of diastereoisomeric diesters with stereogenic centres at C-3 and C-5. The relative stereochemistry of all but two of the products having 1,3-related stereocentres has been proved by silyl-to-hydroxy conversion using mercuric acetate and peracetic acid to give the corresponding alcohols or their derived lactones.An attempt to identify a purely steric rule by which it might be possible to predict which diastereoisomer would be the major product in each of these reactions was based on arguments about, and molecular mechanics calculations of, the lowest-energy conformations of the starting materials. The only rule that emerges is that ketones are regularly attacked in sense B, defined in the drawings 21 and 23, in a conformation that minimises the interaction between the group M on the stereogenic centre and the group R1 on the other side of the ketone, but even within this group of reactions, phenyl groups in either or both locations sometimes lead to anomalies.Krapcho reactions take place more rapidly and in higher yield using four equivalents of lithium chloride in place of the usual sodium chloride, and adding two equivalents of water to the DMSO.
    将 4-苯基戊酸甲酯 25 甲酯化,得到非对映异构体(2RS,4SR )-2-甲基-4-苯基戊酸甲酯 26 和(2RS,4RS)-2-甲基-4-苯基戊酸甲酯 27,比例为 44∶56。3-二甲基(苯基)硅基丁醛 28、3-二甲基(苯基)硅基-3-苯基丙醛 32 和 3-二甲基(苯基)硅基-4-甲基戊醛 36,每种醛的 C-3 上都有一个带有硅基的立体中心,并先后带有一个甲基、一个苯基和一个异丙基、与一系列的甲基、苯基和异丙基亲核物反应,得到一对非对映异构的仲醇 40-42、47-49 和 54-56,它们具有 1,3 个相关的立体中心。同样的醇 43-45、50-52 和 57-59 也可以通过相应的酮 29-31、33-35 和 37-39 与一系列氢化物试剂发生还原反应来制备,其中三个酮 31、35 和 39 与苯基锂发生反应,得到叔醇 46、53 和 60 的混合物。 (E)-和(Z)-α,β-不饱和甲基酯 61、62、64、65、67 和 68 由相同的三种醛与甲氧羰基甲基三苯基膦制备而成,它们与苯基二甲基硅琥珀酸酯试剂和锌酸试剂反应,得到非对映异构的 1,3-二硅烷化酯对。同样,由相同的三种醛与丙二酸二甲酯制备的 α、β-不饱和二甲基二酯 63、66 和 69 与苯基二甲基硅烷基锂及相应的铜酸盐和锌酸盐试剂发生反应,生成一对非对映异构的 1,3-二硅烷基二酯,与各种甲基和苯基亲核剂发生反应,生成相应的一对非对映异构的二酯,其立体中心位于 C-3 和 C-5。除了两种具有 1,3 相关立体中心的产物外,其他所有产物的相对立体化学性质都已通过使用乙酸巯基和过乙酸进行硅基-羟基转换而得到相应的醇或其衍生内酯得到证实。出现的唯一规则是,酮在图 21 和图 23 中定义的 B 意义上经常被攻击,其构象使立体中心上的基团 M 与酮另一侧的基团 R1 之间的相互作用最小,但即使在这组反应中,苯基在任一位置或两个位置有时也会导致异常。
  • Stereocontrolled approach to δ- and γ-lactones and 1,3-diols. The role of X− ion in the selenolactonization
    作者:Michelangelo Gruttadauria、Carmela Aprile、Renato Noto
    DOI:10.1016/s0040-4039(02)00093-x
    日期:2002.2
    Two complementary approaches have been realized for the stereoselective synthesis of 4,6-disubstituted δ-lactones and 1,3-anti and syn diols. In the 6-endo selenolactonization the role of the X− ion on the stereoselectivity is shown. Moreover, the highly stereoselective transformation of the 6-endo δ-lactone to the 5-exo γ-lactone is reported.
    对于4,6-二取代的δ-内酯与1,3-抗和合成二醇的立体选择性合成,已经实现了两种互补的方法。在6-内切selenolactonization的X的作用-显示在立体选择性离子。此外,6-的高度立体选择性转化内切δ内酯到5-外型报道γ内酯。
  • Pharmaceutical composition useful for the treatment of hypercholesteremia
    申请人:Merck & Co., Inc.
    公开号:EP0010299A1
    公开(公告)日:1980-09-17
    Pharmaceutical composition, useful for the treatment of hypercholesteremia in mammals, especially humans, comprising (a) a cholesterol synthesis inhibitor acting at the HMG-CoA reductase level with an EO,. less than 10-°, such as a 6-[2-(8-substituted- 2-methyl-1,2,6,7,8,8a -hexahydro-1-naphthyl) ethyl)-4-hydroxy-4, 5-dihydro-2-pyrone or a 4R trans-6-phenyi-E-4-hydroxytetrahydropyran-2-one in which E is a bond, a C1-) alkylene or-CH =CH- and (b) a non-toxic anion exchange resin in the weight ratio of 1:0.08 to 1:15,000. The resin preferably is a styrene-divinylbenzene copolymer containing quaternary ammonium groups. When present in the indicated weight ratios, synergism exists between the cholesterol synthesis inhibitor and the anion exchange resin. The components can be present separately for separate dosages or, preferably, as a unitary combination. The effects of treatments with compound II (Compacun) and with cholestyramine, separately and in combination, are illustrated by figure 1.
    用于治疗哺乳动物,尤其是人类高胆固醇血症的药物组合物,包括 (a) 在 HMG-CoA 还原酶水平起作用的胆固醇合成抑制剂,其 EO小于 10-°,如 6-[2-(8-取代-2-甲基-1,2,6,7,8,8a-六氢-1-萘基)乙基)-4-羟基-4、5-二氢-2-吡喃酮或 4R 反式-6-苯基-E-4-羟基四氢吡喃-2-酮,其中 E 为键、C1-)亚烷基或-CH =CH- 和 (b) 无毒阴离子交换树脂,重量比为 1:0.08 至 1:15,000 的重量比。树脂最好是含有季铵基团的苯乙烯-二乙烯基苯共聚物。当以所述重量比存在时,胆固醇合成抑制剂和阴离子交换树脂之间会产生协同作用。这些成分可以分别以不同的剂量存在,也可以作为一个整体组合存在。图 1 说明了化合物 II(康帕康)和胆甾胺单独或组合使用的效果。
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