(3S,4S)-4,8-dimethyl-1-phenyl-4-vinylnon-7-en-3-ol | 84363-93-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S,4S)-4,8-dimethyl-1-phenyl-4-vinylnon-7-en-3-ol
• 英文别名: syn-7-Hydroxy-2,6-dimethyl-9-phenyl-6-vinyl-2-nonene；4,8-dimethyl-1-phenyl-4-vinylnon-7-en-3-ol
• CAS: 84363-93-9；84363-94-0
• 化学式: C₁₉H₂₈O
• 分子量: 272.431
• InChiKey: VBKMMIOUGDZBRA-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  neryl chloride 在 三氯硅烷 、 N,N-二异丙基乙胺 、 copper(l) chloride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (3S,4S)-4,8-dimethyl-1-phenyl-4-vinylnon-7-en-3-ol
  参考文献：
  名称：

  通过有机硅中间体从烯丙基氯化物轻松合成双合成和反高烯丙醇

  摘要：

  通过有机硅中间体从烯丙基氯高度区域选择性和非对映选择性合成高烯丙醇。虽然从 (Z)-烯丙基氯制备合成高烯丙醇，但从 (E)-烯丙基氯制备反高烯丙醇。1-Chloro-2,4-pentadiene 在二烯体系的 γ 位置发生区域选择性反应。

  DOI：

  10.1246/cl.1994.1773

文献信息

• A Catalytic Dual Isomerization/Allylboration Sequence for the Stereoselective Construction of Congested Secondary Homoallylic Alcohols
  作者：Yangbin Liu、Clément Mazet

  DOI：10.1021/acs.joc.0c00565

  日期：2020.4.17

  homoallylboronates into (chiral) aldehydes and allylboronates, respectively. In the same flask, a chiral Brønsted acid is added next to engage the isomerization products into a stereocontrolled allylboration reaction. Structural variations have been performed on both the allylic alcohols and the homoallylboronates. This mild process affords an array of stereochemically congested and complex chiral secondary

  报道了具有相邻的季（立体）中心的均烯丙基醇的非对映和对映选择性制备的催化序列。一锅法依赖于使用单个（非手性或手性）铱配合物来催化伯烯丙基醇和高烯丙基硼酸酯的同时异构化为（手性）醛和烯丙基硼酸酯。在同一烧瓶中，接着添加手性布朗斯台德酸，使异构化产物参与立体可控的烯丙基硼化反应。已经对烯丙基醇和高烯丙基硼酸酯进行了结构变化。这种温和的过程以高收率，优异的非对映选择性和通常较高的对映选择性提供了一系列立体化学富集和复杂的手性仲均烯丙基醇。
• STEREOSELECTIVE ACYCLIC SYNTHESIS VIA ALLYLMETALS: STRUCTURAL DEPENDENCE IN A LEWIS-ACID CATALYZED ADDITION OF ALLYLTINS TO ALDEHYDES
  作者：Masato Koreeda、Yoshio Tanaka

  DOI：10.1246/cl.1982.1299

  日期：1982.8.5

  Lewis-acid catalyzed reaction of allyltins with aldehydes at −78 °C provide homoallyl alcohols with high stereoselectivity; 2-alkenyltins in general provide erythro adducts preferentially with an erythro/threo ratio greater than 12/1, whereas only threo adducts can be obtained from E-cinnamyltins.

  路易斯酸催化烯丙基锡与醛在 -78 °C 下的反应提供具有高立体选择性的高烯丙醇；2-烯基锡通常优先提供赤/苏比大于12/1的赤加合物，而从E-肉桂锡只能获得苏加加合物。
• Facile and Highly Stereoselective Synthesis of Homoallylic Alcohols Using Organosilicon Intermediates
  作者：Shu Kobayashi、Koichi Nishio

  DOI：10.1021/jo00101a021

  日期：1994.11

  Allyltrichlorosilanes regioselectively reacted with aldehydes in N,N-dimethylformamide (DMF) without a catalyst to afford the corresponding homoallylic alcohols in high yields. The reactions proceeded under neutral conditions, and syn- and anti-homoallylic alcohols were stereoselectively obtained from (Z)- and (E)-allyltrichlorosilanes, respectively. In these reactions, DMF coordinated to the silicon atom of the allyltrichlorosilanes to form hypervalent silicates, which in turn reacted with aldehydes smoothly. Solvent effects in these reactions were also examined. The reactions were applied to the one-pot synthesis of homoallylic alcohols from allylic chlorides via organosilicon intermediates. While syn-homoallylic alcohols were prepared from (Z)-allyl chlorides, antihomoallylic alcohols were obtained from (E)-allyl chlorides. Unique regioselectivities in the reactions of 1-chloro-2,4-pentadiene were also found. Finally, the one-pot synthesis of homoallylic alcohols from 1,3-dienes is reported.