(1S)-1-[3-[(1S)-1-hydroxypropyl]phenyl]propan-1-ol | 137365-11-8

• 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: (1S)-1-[3-[(1S)-1-hydroxypropyl]phenyl]propan-1-ol
• CAS: 137365-11-8
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: RTTDEYJHLBZVPS-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  间苯二甲醛 、 diethylzinc 在 titanium(IV) isopropylate 、 2,2-dimethyl-α,α,α',α'-tetra(naphth-2-yl)-1,3-dioxolan-4,5-dimethanol 作用下， 以 甲苯 为溶剂， 反应 50.0h， 以95%的产率得到(1S)-1-[3-[(1S)-1-hydroxypropyl]phenyl]propan-1-ol
  参考文献：
  名称：

  Schmidt, Beat; Seebach, Dieter, Angewandte Chemie, 1991, vol. 103, # 10, p. 1383 - 1385

  摘要：

  DOI：

文献信息

• One catalyst for two distinct reactions: sequential asymmetric hetero Diels–Alder reaction and diethylzinc addition
  作者：Haifeng Du、Xue Zhang、Zheng Wang、Kuiling Ding

  DOI：10.1016/j.tet.2005.08.007

  日期：2005.10

  addition to the benzaldehyde, affording the corresponding secondary alcohol with up to 94.5% ee under optimized conditions. On the basis of these facts, the integration of two distinct enantioselective reactions, HDA and diethylzinc addition reactions, has been realized in one-pot with the promotion of a single chiral zinc catalyst in a sequential manner. The impact of diimine additive on the catalytic system

  本文介绍了成功开发出一系列包含（R）-3,3'-Br 2 -BINOL配体和各种二亚胺活化剂的手性锌催化剂，通过组合方法使Danishefsky's二烯与醛的对映选择性HDA反应，得到相应的2 ，3-二氢-4 H-pyran-4-one衍生物，具有出色的收率和对映选择性。这类催化剂的应用范围也扩大到了苯甲醛中的二乙基锌加成反应，从而在优化的条件下得到了相应的仲醇，其ee含量高达94.5％。基于这些事实，已经实现了两个不同的对映选择性反应，即HDA和二乙基锌加成反应的整合，并且以顺序的方式促进了一种手性锌催化剂的整合。通过探索反应体系的非线性效应，研究了二亚胺添加剂对HDA反应催化体系的影响。催化体系中表现出的正非线性效应可归因于杂手性锌物质的不良溶解性。概述了Danishefsky二烯与醛的2- BINOL / Zn /二亚胺催化的对映选择性HDA反应。
• Enantio- and diastereoselective titanium-TADDOLate catalyzed addition of diethyl and bis(3-buten-1-yl) zinc to aldehydes a full account with preparative details
  作者：Dieter Seebach、Albert K. Beck、Beat Schmidt、Yan Ming Wang

  DOI：10.1016/s0040-4020(01)89373-x

  日期：1994.4

  enantioselective addition of alkyl groups from organozinc reagents to aldehydes (19 examples). With 0.05 – 0.20 equiv. of the diisopropoxy-Ti-TADDOLate bearing four 2-naphthyl groups and 1.2 equiv. of Ti(OCHMe2)4 in toluene or ether solution the best results are obtained: ≥ 98 : 2 enantiomer ratios with all types of aldehydes tested (saturated, olefinic, and acetylenic aliphatic, aromatic, and heteroaromatic)

  钛（IV）的α，α，α'，α'-四芳基-2-单-和-2,2-二取代-1,3-二氧戊环-4,5-二甲醇盐（TADDOLates）用于路易斯酸介导的从有机锌试剂到醛的烷基对映选择性加成（19个实例）。当0.05 – 0.20当量。带有四个2-萘基和1.2当量的二异丙氧基-Ti-TADDOLate的盐。在甲苯或乙醚溶液中制备Ti（OCHMe 2）4可获得最佳结果：≥98：2对映体比例，并且测试了所有类型的醛（饱和，烯烃和炔属脂族，芳族和杂芳族）。亲核加成从（发生硅醛的）面时（R，R）-TADDOLate被使用。-使用手性醛，实现了二乙基锌的非对映选择性加成（7个实例）。在醛中不存在另外的官能团的情况下，非对映选择性不依赖于其手性（“试剂对照”，两个实例）。-将对映选择性地向醛中添加二烷基锌试剂的TADDOLate方法与其他路易斯酸或氨基醇介导的方法进行了比较。给出了完整的实验细节以及通过文献分配获得的某些产品的绝对构型的相关性。
• Formation of mixed aryl–, alkyl–lithium aggregates in the heteroatom assisted lithiation of α,α′-dialkyl substituted 1,3-bis[(dimethylamino)methyl]benzene1These results were presented in part at the Symposium `Frontiers in Organometallic Chemistry' at the Spring 1997 American Chemical Society meeting in San Francisco.12Dedicated to Prof. Ken Wade on the occasion of his 65th birthday, thanking him for his `rules', discussions and long friendship.2
  作者：Johannes G. Donkervoort、José L. Vicario、Evelien Rijnberg、Johann T.B.H. Jastrzebski、Huub Kooijman、Anthony L. Spek、Gerard van Koten

  DOI：10.1016/s0022-328x(97)00554-8

  日期：1998.1

  The heteroatom assisted lithiation of 1,3-bis[1-(dimethylamino)ethyl]benzene with n-BuLi afforded 2,6-bis[1-(dimethylamino)ethyl]phenyllithium. An X-ray crystal structure determination revealed a dimeric aggregate in which the four benzylic chiral centers are identical, pointing to stereoselective crystallization. In contrast, reaction of 1,3-bis[1-(dimethylamino)propyl]benzene with n-BuLi afforded a dimeric aggregate comprising the parent lithiated compound and n-BuLi in a 1:1 molar ratio. The four Li atoms and the four bridging carbon atoms are arranged in a unique ladder-type C-Li-2-C-2'-Li-2-C framework. (C) 1998 Elsevier Science S.A.
• Schmidt, Beat; Seebach, Dieter, Angewandte Chemie, 1991, vol. 103, # 10, p. 1383 - 1385
  作者：Schmidt, Beat、Seebach, Dieter

  DOI：——

  日期：——