anti-3-phenyl-4-hydroxy-1-pentene | 40596-14-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: anti-3-phenyl-4-hydroxy-1-pentene
• 英文别名: (2RS,3RS)-3-phenyl-4-penten-2-ol；anti-3-phenylpent-4-en-2-ol；(2S,3S)-3-phenylpent-4-en-2-ol
• CAS: 40596-14-3；84363-85-9；84391-11-7；124844-76-4
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: QUYXSTRLUCBEDX-GXSJLCMTSA-N

物化性质

• 沸点：
  251.4±9.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  anti-3-phenyl-4-hydroxy-1-pentene 在 potassium permanganate 、 sodium periodate 作用下， 生成 erythro-3-Hydroxy-2-phenylbuttersaeure
  参考文献：
  名称：

  Erythroselectivity in addition of γ-substituted allylsilanes to aldehydes in the presence of titanium chloride

  摘要：

  DOI：

  10.1016/s0040-4039(00)88045-4
• 作为产物：
  描述：

  (Z)-β-bromostyrene 在 titanium chloride 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 anti-3-phenyl-4-hydroxy-1-pentene
  参考文献：
  名称：

  Erythroselectivity in addition of γ-substituted allylsilanes to aldehydes in the presence of titanium chloride

  摘要：

  DOI：

  10.1016/s0040-4039(00)88045-4

文献信息

• Copper-Catalyzed Enantiotopic-Group-Selective Allylation of <i>gem</i>-Diborylalkanes
  作者：Minjae Kim、Bohyun Park、Minkyeong Shin、Suyeon Kim、Junghoon Kim、Mu-Hyun Baik、Seung Hwan Cho

  DOI：10.1021/jacs.0c11750

  日期：2021.1.20

  We report a copper-catalyzed enatiotopic-group-selective allylation of gem-diborylalkanes with allyl bromides. The combination of copper(I) bromide and H8-BINOL derived phosphoramidite ligand proved to be the most effective catalytic system to provide various enantioenriched homoallylic boronate esters, containing a boron-substituted stereogenic center that is solely derived from gem-diborylalkanes

  我们报告了铜催化的对映基团选择性烯丙基化的 gem-二硼烷烃与烯丙基溴。溴化铜 (I) 和 H8-BINOL 衍生的亚磷酰胺配体的组合被证明是提供各种对映体富集的高烯丙基硼酸酯的最有效的催化系统在温和条件下具有高对映体比率。已经进行了实验和理论研究以阐明反应机理，揭示了宝石-二硼烷基烷烃与手性铜配合物的对映基团选择性转移金属是如何发生手性 α-硼烷基-铜物种的。还包括合成各种手性构件的其他合成应用。
• Allylic tin(IV)-tin(II) chloride-acetonitrile as a novel system for allylation of carbonyls or imines
  作者：Makoto Yasuda、Yoshihiro Sugawa、Akihiro Yamamoto、Ikuya Shibata、Akio Baba

  DOI：10.1016/0040-4039(96)01285-3

  日期：1996.8

  Effective allylation of aldehydes, ketones and imines was accomplished by allylic tributyltins 1 in the presence of SnCl2 in an acetonitrile solution. In this reaction system. Sn(IV)Sn(II) transmetallation must play a key role, generating the allylic tin(II) reagents as a novel reacting species. Acetonitrile effectively promoted the transmetallation to give anti-adducts in the reaction with cinnamyltin

  醛，酮和亚胺的有效烯丙基化是通过在乙腈溶液中存在SnCl 2的情况下，通过烯丙基三丁基锡1来实现的。在这个反应体系中。Sn（IV）Sn（II）的金属转移作用必须发挥关键作用，生成烯丙基锡（II）试剂作为一种新型反应物种。乙腈在与肉桂酸锡1c的反应中有效地促进了金属转移，产生了反加合物，而二氯甲烷则干扰了金属转移生成了顺式加合物。
• Iridium-Catalyzed Coupling Reaction of Primary Alcohols with 1-Aryl-1-propynes Leading to Secondary Homoallylic Alcohols
  作者：Yasushi Obora、Shintaro Hatanaka、Yasutaka Ishii

  DOI：10.1021/ol901366q

  日期：2009.8.6

  We report iridium-catalyzed coupling of 2-alkynes such as 1-aryl-1-propynes with primary alcohols leading to secondary homoallylic alcohols as products. This reaction involves an iridium-catalyzed novel catalytic transformation of 2-alkynes and primary alcohols through the formation of hydrido(π-allyl)iridium as a possible key intermediate.

  我们报道了铱催化的2-炔烃（例如1-芳基-1-丙炔）与伯醇的偶合，从而导致仲均烯丙基醇成为产物。该反应涉及通过氢化（π-烯丙基）铱作为可能的关键中间体的铱催化的2-炔烃和伯醇的新型催化转化。
• Hydroboration of mono-substituted allenes: A general synthetic route to the higher crotylboranes and anti-3-alkyl/aryl-4-hydroxy-1-alkenes
  作者：Gowriswari Narla、Herbert C. Brown

  DOI：10.1016/s0040-4039(96)02255-1

  日期：1997.1

  Hydroboration of mono-substituted allenes with Chx2BH at 0 °C leads to the corresponding (E)-substituted allylboranes, known as higher crotylboranes, exclusively. These higher crotylboranes react with aldehydes, and on oxidation, provide the corresponding anti-3-alkyl/aryl-4-hydroxy-1-alkenes in high diastereomeric excess. By changing the hydroborating reagent to dIpc2BH, synthesis of the corresponding

  在0°C下用Chx 2 BH对单取代的烯基进行硼氢化反应，会单独生成相应的（E）取代的烯丙基硼烷，称为高级巴豆基硼烷。这些高级巴豆基硼烷与醛反应，并在氧化时以非对映异构体过量的形式提供相应的抗-3-烷基/芳基-4-羟基-1-烯烃。通过将硼氢化试剂改变为d Ipc 2 BH，可以以优异的非对映选择性和良好的对映选择性实现相应的旋光性抗-3-烷基/芳基-4-羟基-1-烯烃的合成。
• Stereoselective synthesis of allylic boronates via palladium-catalyzed cross-coupling reaction of Knochel's (dialkoxyboryl) methylzinc reagents with 1-halo-1-alkenes
  作者：Takeo Watanabe、Norio Miyaura、Akira Suzuki

  DOI：10.1016/0022-328x(93)83081-6

  日期：1993.2

  The cross-coupling reaction of (dialkoxyboryl)methylzinc reagents IZnCH2B(OR)2 with 1-halo-1-alkenes was catalysed by triphenyl-phosphine- or triphenylarsine-based palladium complexes to provide esters of stereodefined allylboronic acids with stereoselectivity. The reaction was applied to provide a cyclic alcohol via the first intramolecular allylboration of carbonyl.

  三苯基膦或三苯基ar基钯配合物催化（二烷氧基硼基）甲基锌试剂IZnCH 2 B（OR）2与1-卤代-1-烯烃的交叉偶联反应，从而提供具有立体选择性的立体定义的烯丙基硼酸的酯。通过羰基的第一次分子内烯丙基硼化反应以提供环状醇。