(2S,3S)-1,3-dihydroxy-2-methyl-5-phenyl-4-pentene | 95585-63-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (2S,3S)-1,3-dihydroxy-2-methyl-5-phenyl-4-pentene
• 英文别名: (2S,3S,E)-2-methyl-5-phenylpent-4-ene-1,3-diol；(E,2S,3S)-2-methyl-5-phenylpent-4-ene-1,3-diol
• CAS: 95585-63-0
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: JNFCGBNYOJIKHB-HUAGXHDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-1,3-dihydroxy-2-methyl-5-phenyl-4-pentene 在 4-二甲氨基吡啶 、 二异丁基氢化铝 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 64.0h， 生成 (3S,4R,E)-4-(benzyloxy)-3-methyl-6-phenylhex-5-enenitrile
  参考文献：
  名称：

  来自线性前体的多环分子：克拉沃宁和相关复杂结构的立体选择性合成。

  摘要：

  DOI：

  10.1002/anie.200502296
• 作为产物：
  描述：

  ethyl 2-methyl-3-oxo-5-phenylpent-4-enoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (2S,3S)-1,3-dihydroxy-2-methyl-5-phenyl-4-pentene
  参考文献：
  名称：

  The absolute configuration of oudemansin total synthesis of (−)-oudemansin

  摘要：

  DOI：

  10.1016/s0040-4039(00)81829-8

文献信息

• Methods for the Preparation of Thiazolidinethione Indene-Based Chiral Auxiliaries
  申请人：Olivo Horacio F.

  公开号：US20100179330A1

  公开（公告）日：2010-07-15

  Methods for the preparation of indene-based thiazolidinethiones are provided comprising contacting 1-amino-2,3-dihydro-1H-inden-2-ol, or a substituted derivative thereof, with an acid under suitable reaction conditions to provide a first intermediate; and contacting the first intermediate with an alkali xanthate in the presence of an alkali hydroxide under suitable reaction conditions to provide a compound of formula (III), wherein R 1 -R 8 are defined herein.

  提供了一种制备基于茚的噻唑啉硫酮的方法，包括将1-氨基-2,3-二氢-1H-茚-2-醇或其取代衍生物与酸在适当的反应条件下接触，以提供第一中间体；并在适当的反应条件下将第一中间体与碱性黄原酸酯在碱性羟化物存在下接触，以提供式（III）的化合物， 其中R1-R8在此处定义。
• Indene-Based Thiazolidinethione Chiral Auxiliary for Propionate and Acetate Aldol Additions
  作者：Antonio Osorio-Lozada、Horacio F. Olivo

  DOI：10.1021/ol702980p

  日期：2008.2.1

  An indene-based thiazolidinethione chiral auxiliary was prepared in two steps from trans-1-amino-2-indanol. Chlorotitanium enolates of this chiral auxiliary delivered excellent diastereoselectivities in propionate and acetate aldol additions. The chiral auxiliary was easily removed to deliver several valuable functionalities.
• Diastereoselective synthesis of an advanced intermediate of the crocacin family using asymmetric transfer hydrogenation-DKR and Marshall allenylation as key reactions
  作者：Gullapalli Kumaraswamy、Vykunthapu Narayanarao、Prakash Shanigaram、Guniganti Balakishan

  DOI：10.1016/j.tet.2015.09.057

  日期：2015.11

  The natural product of a crocacin-family structural scaffold bearing consecutive anti-anti-syn stereogenic centers was accomplished by means of ATH-DKR and Marshall allenylation reactions with high stereo-control levels. The salient feature of this process is that a single catalytic asymmetric Ru-complex was used for the chirality genesis of pivotal reactions with a high substrate-to-catalyst ratio. (C) 2015 Elsevier Ltd. All rights reserved.
• Total synthesis of (-oudemansin
  作者：Tadashi Nakata、Takaaki Kuwabara、Yōichirō Tani、Takeshi Oishi

  DOI：10.1016/s0040-4039(00)87009-4

  日期：1982.1
• US8309738B2
  申请人：——

  公开号：US8309738B2

  公开（公告）日：2012-11-13