(R)-(E)-2,4-dimethyl-1-phenyl-pent-1-en-3-ol | 512785-78-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (R)-(E)-2,4-dimethyl-1-phenyl-pent-1-en-3-ol
• 英文别名: (1E,3R)-2,4-Dimethyl-1-phenyl-1-penten-3-ol；(E,3R)-2,4-dimethyl-1-phenylpent-1-en-3-ol
• CAS: 512785-78-3
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: QVGDJCIWHDWTCP-YGNAEDSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  1-苯基-1-丙炔 、 异丁醛 在 1,3-二甲基-2-咪唑啉酮 、 bis(1,5-cyclooctadiene)nickel (0) 、 三乙基硼 、 (S)-(+)-2-异丙基-5-甲基二苯磷 作用下， 以 乙酸乙酯 为溶剂， 反应 44.0h， 以95%的产率得到(R)-(E)-2,4-dimethyl-1-phenyl-pent-1-en-3-ol
  参考文献：
  名称：

  (S)-(+)-NEOMENTHYLDIPHENYLPHOSPHINE IN NICKEL-CATALYZED ASYMMETRIC REDUCTIVE COUPLING OF ALKYNES AND ALDEHYDES: ENANTIOSELECTIVE SYNTHESIS OF ALLYLIC ALCOHOLS AND a-HYDROXY KETONES

  摘要：

  DOI：

  10.15227/orgsyn.084.0111

文献信息

• Highly Regio- and Enantioselective Reductive Coupling of Alkynes and Aldehydes via Photoredox Cobalt Dual Catalysis
  作者：Yan-Lin Li、Shi-Qi Zhang、Jie Chen、Ji-Bao Xia

  DOI：10.1021/jacs.1c03527

  日期：2021.5.19

  A Co-catalyzed highly regio- and enantioselective reductive coupling of alkynes and aldehydes has been developed under visible light photoredox dual catalysis. A variety of enantioenriched allylic alcohols have been obtained by using unsymmetrical internal alkynes and commercially available catalyst, chiral ligand, and reagents. It is noteworthy that this approach has considerable advantages, such

  在可见光光氧化还原双催化下开发了一种共催化的炔烃和醛的高度区域选择性和对映选择性还原偶联。通过使用不对称内部炔烃和市售催化剂、手性配体和试剂，已经获得了多种对映体富集的烯丙醇。值得注意的是，这种方法具有相当大的优势，例如出色的区域-（> 40 个示例> 95:5）、立体-（高达> 95:5 E / Z）和对映选择性（92-99% ee，> 35个例子）控制，反应条件温和，底物范围广，官能团相容性好，使其对映选择性炔-醛还原偶联反应有了很大的改进。
• Enantioselective acyl transfer catalysts and their use in kinetic resolution of alcohols and desymmetrization of meso-diols
  申请人：Birman Vladimir

  公开号：US20050256150A1

  公开（公告）日：2005-11-17

  Novel enantioselective acylation catalysts comprising chiral derivatives of DHIP and DHIQ, having the following representative general structures are disclosed: These new compounds are useful for resolving racemates or further enhancing the enantiomeric excess of an enantiomerically enriched composition and for desymmetrizing meso compounds.

  新型对映选择性酰化催化剂包括手性的DHIP和DHIQ衍生物，具有以下代表性的一般结构：这些新化合物可用于分离外消旋体或进一步增强对映体富集组合物的对映过量，并用于非对称化中间体化合物。
• Catalytic Asymmetric Reductive Coupling of Alkynes and Aldehydes:  Enantioselective Synthesis of Allylic Alcohols and α-Hydroxy Ketones
  作者：Karen M. Miller、Wei-Sheng Huang、Timothy F. Jamison

  DOI：10.1021/ja034366y

  日期：2003.3.1

  enantioselective method for catalytic reductive coupling of alkynes and aldehydes is described. Allylic alcohols are afforded with complete E/Z selectivity, generally >95:5 regioselectivity, and in up to 96% ee. In conjunction with ozonolysis, this process is complementary to existing methods of enantioselective alpha-hydroxy ketone synthesis.

  描述了一种用于炔烃和醛类催化还原偶联的高度对映选择性方法。烯丙醇具有完全的 E/Z 选择性，通常 > 95:5 区域选择性，以及高达 96% 的 ee。结合臭氧分解，该过程是对映选择性α-羟基酮合成现有方法的补充。
• Kinetic Resolution of Alcohols Using a 1,2-Dihydroimidazo[1,2-<i>a</i>]quinoline Enantioselective Acylation Catalyst
  作者：Vladimir B. Birman、Hui Jiang

  DOI：10.1021/ol051063v

  日期：2005.8.1

  [GRAPHICS]A new enantioselective acylation catalyst (CI-PIO), designed to provide enhanced T-stacking with benzylic and cinnamyl alcohol substrates, was found to give considerably increased reaction rates and selectivities compared with the first-generation catalyst CF3-PIP.
• (S)-(+)-NEOMENTHYLDIPHENYLPHOSPHINE IN NICKEL-CATALYZED ASYMMETRIC REDUCTIVE COUPLING OF ALKYNES AND ALDEHYDES: ENANTIOSELECTIVE SYNTHESIS OF ALLYLIC ALCOHOLS AND a-HYDROXY KETONES
  作者：van Dyke, Aaron R.、Miller, Karen M.、Jamison, Timothy F.、Fleming, Matthew J.、Lautens, Mark

  DOI：10.15227/orgsyn.084.0111

  日期：——