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(2S,6S,10R,14R)-16-[(S)-2-Benzyloxy-1-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-16-oxo-hexadecyloxymethyl)-ethoxy]-2,6,10,14-tetramethyl-hexadecanal | 156593-03-2

中文名称
——
中文别名
——
英文名称
(2S,6S,10R,14R)-16-[(S)-2-Benzyloxy-1-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-16-oxo-hexadecyloxymethyl)-ethoxy]-2,6,10,14-tetramethyl-hexadecanal
英文别名
(2S,6S,10R,14R)-2,6,10,14-tetramethyl-16-[(2S)-3-phenylmethoxy-2-[(3R,7R,11S,15S)-3,7,11,15-tetramethyl-16-oxohexadecoxy]propoxy]hexadecanal
(2S,6S,10R,14R)-16-[(S)-2-Benzyloxy-1-((3R,7R,11S,15S)-3,7,11,15-tetramethyl-16-oxo-hexadecyloxymethyl)-ethoxy]-2,6,10,14-tetramethyl-hexadecanal化学式
CAS
156593-03-2
化学式
C50H90O5
mdl
——
分子量
771.262
InChiKey
XIUDSSAIYQTASQ-SRCPAQCLSA-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

计算性质

  • 辛醇/水分配系数(LogP):
    16.2
  • 重原子数:
    55
  • 可旋转键数:
    39
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.84
  • 拓扑面积:
    61.8
  • 氢给体数:
    0
  • 氢受体数:
    5

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

  • Total Synthesis of Archaeal 36-Membered Macrocyclic Diether Lipid
    作者:Tadashi Eguchi、Kenji Arakawa、Takumi Terachi、Katsumi Kakinuma
    DOI:10.1021/jo962327h
    日期:1997.4.1
    2 is reported. The synthesis is based upon stereoselective preparation of functionalized isoprenoid chains, ether-linkage formation between the isoprenoid chains with a glycerol derivative, and the ultimate intramolecular dicarbonyl coupling using low-valent titanium known as McMurry coupling. This synthetic method has successfully provided the first practical route to chemically defined archaeal macrocyclic
    报道了古细菌36元大环二醚脂质2的全合成。合成基于功能性异戊二烯链的立体选择性制备,异戊二烯链与甘油衍生物之间的醚键形成以及使用低价钛的最终分子内二羰基偶联(称为McMurry偶联)。这种合成方法成功地提供了化学上确定的古细菌大环膜脂质的第一个实用途径,由于缺乏合成途径,这些脂质无法获得。还描述了立体化学均一的古细菌双二十烷酰基甘油脂质的高度立体选择性和便利的合成。
  • An Olefin Metathesis Approach to 36- and 72-Membered Archaeal Macrocyclic Membrane Lipids
    作者:Kenji Arakawa、Tadashi Eguchi、Katsumi Kakinuma
    DOI:10.1021/jo980472k
    日期:1998.7.1
    An olefin metathesis approach, which has been successfully applied to an efficient synthesis of archaeal 36- and 72-membered macrocyclic membrane lipids (1, 2a, and 2b), is reported. In the presence of a Grubbs' ruthenium-alkylidene complex, RuCl2(=CHPh)(PCy3)(2) (3), a ring-closing metathesis (RCM) reaction of alpha,omega-diene 5 efficiently proceeded in 79% yield under high dilution conditions to give 36-membered 6. By changing the reaction conditions, a acyclic diene metathesis (ADM) product 7 was predominantly formed from the same substrate 5. The acyclic product 7 was subsequently subjected to the RCM reaction under high dilution conditions to provide 72-membered compound 8 in 45% yield. Final catalytic hydrogenation of 6 and 8 afforded the 36-membered lipid I and a mixture of the 72-membered lipid 2a and 2b, respectively. The present synthetic method appears to be of significant advantage for the synthesis of such giant ring structures of the 36- and 72-membered lipids, because both of the macrocylic lipids can be obtained in a short step at will from the same starting material only by changing the order and conditions of the metathesis reaction.
  • The first synthesis of an archaebacterial 36-membered macrocyclic diether lipid
    作者:Tadashi Eguchi、Takumi Terachi、Katsumi Kakinuma
    DOI:10.1039/c39940000137
    日期:——
    The archaebacterial macrocyclic diether lipid featuring a 36-membered ring is synthesized by the McMurry coupling as a key step.
    关键步骤是通过麦克马里偶联合成具有 36 元环的古细菌大环二元脂。
  • Asymmetric synthesis of cyclo-archaeol and β-glucosyl cyclo-archaeol
    作者:Catalina Ferrer、Peter Fodran、Santiago Barroso、Robert Gibson、Ellen C. Hopmans、Jaap Sinninghe Damsté、Stefan Schouten、Adriaan J. Minnaard
    DOI:10.1039/c3ob27277j
    日期:——
    An efficient asymmetric synthesis of cyclo-archaeol and β-glucosyl cyclo-archaeol is presented employing catalytic asymmetric conjugate addition and catalytic epoxide ring opening as the key steps. Their occurrence in deep sea hydrothermal vents has been confirmed by chromatographic comparison with natural samples.
    本文以催化不对称共轭加成和催化环氧化物开环反应为关键步骤,对环古细菌素和β-葡萄糖基环古细菌素进行了有效的不对称合成。通过与天然样品的色谱比较,证实了它们在深海热液喷口中的存在。
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同类化合物

(5β,6α,8α,10α,13α)-6-羟基-15-氧代黄-9(11),16-二烯-18-油酸 (3S,3aR,8aR)-3,8a-二羟基-5-异丙基-3,8-二甲基-2,3,3a,4,5,8a-六氢-1H-天青-6-酮 (2Z)-2-(羟甲基)丁-2-烯酸乙酯 (2S,4aR,6aR,7R,9S,10aS,10bR)-甲基9-(苯甲酰氧基)-2-(呋喃-3-基)-十二烷基-6a,10b-二甲基-4,10-dioxo-1H-苯并[f]异亚甲基-7-羧酸盐 (+)顺式,反式-脱落酸-d6 龙舌兰皂苷乙酯 龙脑香醇酮 龙脑烯醛 龙脑7-O-[Β-D-呋喃芹菜糖基-(1→6)]-Β-D-吡喃葡萄糖苷 龙牙楤木皂甙VII 龙吉甙元 齿孔醇 齐墩果醛 齐墩果酸苄酯 齐墩果酸甲酯 齐墩果酸乙酯 齐墩果酸3-O-alpha-L-吡喃鼠李糖基(1-3)-beta-D-吡喃木糖基(1-3)-alpha-L-吡喃鼠李糖基(1-2)-alpha-L-阿拉伯糖吡喃糖苷 齐墩果酸 beta-D-葡萄糖酯 齐墩果酸 beta-D-吡喃葡萄糖基酯 齐墩果酸 3-乙酸酯 齐墩果酸 3-O-beta-D-葡吡喃糖基 (1→2)-alpha-L-吡喃阿拉伯糖苷 齐墩果酸 齐墩果-12-烯-3b,6b-二醇 齐墩果-12-烯-3,24-二醇 齐墩果-12-烯-3,21,23-三醇,(3b,4b,21a)-(9CI) 齐墩果-12-烯-3,11-二酮 齐墩果-12-烯-2α,3β,28-三醇 齐墩果-12-烯-29-酸,3,22-二羟基-11-羰基-,g-内酯,(3b,20b,22b)- 齐墩果-12-烯-28-酸,3-[(6-脱氧-4-O-b-D-吡喃木糖基-a-L-吡喃鼠李糖基)氧代]-,(3b)-(9CI) 鼠特灵 鼠尾草酸醌 鼠尾草酸 鼠尾草酚酮 鼠尾草苦内脂 黑蚁素 黑蔓醇酯B 黑蔓醇酯A 黑蔓酮酯D 黑海常春藤皂苷A1 黑檀醇 黑果茜草萜 B 黑五味子酸 黏黴酮 黏帚霉酸 黄黄质 黄钟花醌 黄质醛 黄褐毛忍冬皂苷A 黄蝉花素 黄蝉花定