4-cyclohexyl-1-phenylbuta-2,3-dien-1-ol | 1028375-29-2

• 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: 4-cyclohexyl-1-phenylbuta-2,3-dien-1-ol
• CAS: 1028375-29-2
• 化学式: C₁₆H₂₀O
• 分子量: 228.334
• InChiKey: ZWDBCUMVMWGSMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-cyclohexyl-4-(N,N-dicyclohexylamino)-1-phenylbut-2-yn-1-ol 在 palladium diacetate 、 1,2-双(二五氟代苯基磷基)-乙烷 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以38%的产率得到4-cyclohexyl-1-phenylbuta-2,3-dien-1-ol
  参考文献：
  名称：

  通过钯催化的氢化物转移反应，由炔丙基胺合成单和1,3-二取代的烯丙基。

  摘要：

  由相应的炔丙基胺经钯催化的氢化物转移反应合成了单-和1,3-二取代的烯丙基。在当前的转化中，炔丙基胺可以作为烯丙基阴离子当量处理，并引入各种亲电试剂中，以在钯催化的条件下转化为烯丙基。

  DOI：

  10.1039/b718298h

文献信息

• Copper (I) Iodide-Catalyzed One-Step Preparation of Functionalized Allenes from Terminal Alkynes: Amine Effect
  作者：Jinqiang Kuang、Hongwen Luo、Shengming Ma

  DOI：10.1002/adsc.201100772

  日期：2012.3.16

  An efficient one‐step synthesis of functionalized allenes from readily available functionalized terminal alkynes and aldehydes by applying the effect of a dialkylamine has been developed. The protocol is catalyzed by copper(I) iodide and the dialkylamine is believed to play a very important role in the transformation.

  通过利用二烷基胺的作用，已经开发了从容易获得的官能化末端炔烃和醛类有效地一步合成官能化丙二烯的方法。该方案由碘化亚铜（I）催化，据信二烷基胺在转化中起着非常重要的作用。
• PROCESS FOR SYNTHESIZING HIGHLY OPTICALLY ACTIVE 1,3-DISUBSTITUTED ALLENES
  申请人：ZHEJIANG UNIVERSITY

  公开号：US20160185812A1

  公开（公告）日：2016-06-30

  The present invention relates to a process for efficiently synthesizing highly optically active 1,3-disubstituted allenes, i.e., a one-step process for preparing highly optically active 1,3-disubstituted allenes by using a functionalized terminal alkyne, an aldehyde and a chiral α,α-diphenyl prolinol as reactants under the catalysis of a divalent copper salt. The operation of the process is simple, and the raw materials and reagents are readily available. The process has a broad-spectrum of substrates and a good compatibility for a wide variety of functional groups such as glycosidic units, primary alcohols, secondary alcohols, tertiary alcohols, amides, malonates, etc., and does not require the protection for the functional groups. The obtained axially chiral allene has a moderate to high yield and a good diastereoselectivity or enantioselectivity.

  本发明涉及一种高效合成高度光学活性的1,3-二取代烯烃的方法，即利用功能化末端炔烃、醛和手性α，α-二苯基丙氨醇作为反应物，在二价铜盐催化下制备高度光学活性的1,3-二取代烯烃的一步法过程。该过程操作简单，原材料和试剂易得。该过程具有广泛的底物范围，对各种功能基团如糖苷基、一级醇、二级醇、三级醇、酰胺、马隆酸等具有良好的兼容性，并且不需要对功能基团进行保护。所得的轴向手性烯烃产率中等到高，具有良好的对映选择性或对映选择性。
• OPTICALLY ACTIVE AXIALLY CHIRAL ALPHA-ALLENIC ALCOHOL, SYNTHESIS METHOD AND USE THEREOF
  申请人：SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY, CHINESE ACADEMY OF SCIENCES

  公开号：US20150105567A1

  公开（公告）日：2015-04-16

  The present invention relates to an optically active axially chiral α-allenic alcohol, a synthetic method and use thereof. A method of preparing a high optically active chiral α-allenic alcohol by using propargyl alcohol, aldehyde and chiral α,α-diphenyl-L-prolinol under the protection of tert-butyldimethylsilyl with a mediator zinc bromide. The axially chiral α-allenic alcohol has the structural formula (I). The method of the present invention has the following advantages: the synthesis route is short, operations are simple, raw materials are readily available, separation and purification are convenient, the substrate has high generality, the total yield is high, and enantioselectivity and diastereoselectivity are high. The high optically active axially chiral α-allenic alcohol synthesized by adopting the method of the present invention can conveniently synthesize 2,5-dihydrofuran compounds having central chirality via complete chirality transfer, and at the same time can further be used to synthesize axially chiral allenic amine and allenic malonate compounds without reacemization.

  本发明涉及一种光学活性轴向手性α-亚烯醇，其合成方法和用途。通过在叔丁基二甲基硅保护下使用丙炔醇、醛和手性α,α-二苯基-L-脯氨醇，在锌溴化物介质的保护下制备高光学活性手性α-亚烯醇的方法。轴向手性α-亚烯醇的结构式为（I）。本发明的方法具有以下优点：合成路线短，操作简单，原料易得，分离和纯化方便，底物通用性高，总收率高，并且对映选择性和对映异构选择性高。采用本发明方法合成的高光学活性轴向手性α-亚烯醇可以通过完全手性转移方便地合成具有中心手性的2,5-二氢呋喃化合物，同时还可以进一步用于合成轴向手性亚烯胺和亚烯丙二酸酯化合物而不发生消旋。
• US9701601B2
  申请人：——

  公开号：US9701601B2

  公开（公告）日：2017-07-11