(R)-1-phenyldecanol | 256378-51-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-1-phenyldecanol
• 英文别名: (R)-1-phenyldecan-1-ol；(R)-1-phenyl-1-decanol；(1R)-1-phenyldecan-1-ol
• CAS: 256378-51-5
• 化学式: C₁₆H₂₆O
• 分子量: 234.382
• InChiKey: MRZGGLIGGZHSBZ-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  17.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  癸醛 、 苯基溴化镁 在 aluminum (III) chloride 、 双二甲胺基乙基醚 、 titanium(IV)isopropoxide 、 (R)-5,5',6,6',7,7',8,8'-八氢-[1,1'-联萘]-2,2'-二酚 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以91%的产率得到(R)-1-phenyldecanol
  参考文献：
  名称：

  AlCl3和BDMAEE：一对有效的芳基格氏试剂和醛的高催化不对称芳构化反应活性调节剂

  摘要：

  廉价，节能且适用：借助AlCl 3和BDMAEE [2,2'-氧双（N，N-二甲基乙胺）]，在温和条件下，将各种芳基格氏试剂高度不对称催化加成到醛中用易于制备的（S）-H 8 -BINOL和便宜的市售Ti（O i Pr）4（参见方案），该反应可以轻松扩大规模，而不会损失收率和对映选择性。

  DOI：

  10.1002/chem.201000974

文献信息

• Catalytic asymmetric arylation of aliphatic aldehydes using a B/Zn exchange reaction
  作者：Andressa M.M. Carlos、Maria Eduarda Contreira、Bruna S. Martins、Maira F. Immich、Angélica V. Moro、Diogo S. Lüdtke

  DOI：10.1016/j.tet.2015.01.014

  日期：2015.2

  the arylation of aliphatic aldehydes using the boron/zinc exchange reaction for the generation of transferable aryl groups, in the presence of chiral amino alcohol ligands. For the first time, a systematic investigation of this reaction using aliphatic aldehydes was developed and we have found that it proved to be significantly more challenging than the arylation of aromatic aldehydes. The corresponding

  在本文中，我们描述了在手性氨基醇配体存在下，使用硼/锌交换反应生成可转移芳基的脂族醛的芳基化反应。首次对使用脂肪族醛的反应进行了系统的研究，我们发现与芳香族醛的芳基化反应相比，它具有更大的挑战性。所获得的相应的手性仲醇含量高达73％ee。
• The inexpensive additive <i>N</i> -methylmorpholine effectively decreases the equivalents of nucleophiles in the catalytic highly enantioselective arylation of aryl aldehydes
  作者：Pei Wang、Yue Liu、Ya-Lun Zhang、Chao-Shan Da

  DOI：10.1002/chir.22709

  日期：2017.8

  Highly enantioselective arylation of aryl aldehydes catalyzed by (S)‐H8‐BINOL‐Ti(Oi‐Pr)2 complex in the presence of N‐methylmorpholine (NMM) as an effective and inexpensive additive is described for the first time. We found high enantioselectivity and yield but successfully reduced the equivalents of nucleophiles triarylaluminums by 50% compared with our previous report. The practicability of the process

  首次描述了在有效的，廉价的N-甲基吗啉存在下，由（S）-H 8 -BINOL-Ti（O i - Pr）2络合物催化的芳醛的高度对映选择性芳基化反应。我们发现对映选择性和产率很高，但与我们以前的报告相比，亲核试剂三芳基铝的当量成功降低了50％。由此大大提高了该方法的实用性。
• Chiral synthesis via organoboranes. 14. Selective reductions. 41. Diisopinocampheylchloroborane, an exceptionally efficient chiral reducing agent
  作者：Herbert C. Brown、J. Chandrasekharan、P. V. Ramachandran

  DOI：10.1021/ja00213a030

  日期：1988.3
• Aryl Bromides as Inexpensive Starting Materials in the Catalytic Enantioselective Arylation of Aryl Aldehydes: The Additive TMEDA Enhances the Enantioselectivity
  作者：Yong-Xin Yang、Yue Liu、Lei Zhang、Yan-E Jia、Pei Wang、Fang-Fang Zhuo、Xian-Tao An、Chao-Shan Da

  DOI：10.1021/jo502070r

  日期：2014.11.7

  We used aryl bromides as inexpensive starting materials to enantioselectively arylate aldehydes in one pot. Aryl bromides readily transfer aryls to aryllithiums with n-butyllithium, successively to triarylaluminums with aluminum chloride, and then to aryltitaniums with titanium isopropoxide. Finally aryltitaniums arylate aldehydes catalyzed by (S)-H-8-BINOLTi(Oi-Pr)(2) in excellent yields and enantioselectivities. The additive TMEDA evidently suppresses the racemic background reaction promoted by LiCl generated from salt metathesis. This procedure represents a cost-effective and operationally convenient method for enantioenriched diarylmethanols.