2-(benzyloxy)hexan-1-ol | 141554-36-1

• 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: 2-(benzyloxy)hexan-1-ol
• 英文别名: 2-Phenylmethoxyhexan-1-ol
• CAS: 141554-36-1
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: KEPUSUKIQYZAJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  15.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(benzyloxy)hexan-1-ol 生成 α-benzyloxyhexanal
  参考文献：
  名称：

  Concentration effects in chelation controlled reactions

  摘要：

  The diastereoselectivities of addition reactions of allyltrimethylsilane to an alpha-benzyloxyaldehyde were found to be relatively insensitive to the amount of added TiCl4, and to the absolute concentration of the 1:1 aldehyde/TiCl4 complex. In contrast, diastereoselectivities of similar additions to a structurally related beta-benzyloxyaldehyde were highly dependent on these variables.

  DOI：

  10.1016/0040-4039(95)01897-q
• 作为产物：
  描述：

  2-羟基己酸甲酯 在 lithium aluminium tetrahydride 、 四丁基碘化铵 、 sodium hydride 作用下， 以 乙醚 为溶剂， 反应 28.5h， 生成 2-(benzyloxy)hexan-1-ol
  参考文献：
  名称：

  High diastereoselection in the aldol reaction of the bistrimethylsilyl enol ether of methyl acetoacetate with 2-benzyloxyhexanal: synthesis of (–)-pestalotin

  摘要：

  Aldol condensation of the bistrimethylsilyl enol ether of methyl acetoacetate, compound 2, with 2-benzyloxyhexanal 3c affords highly selectively (99:1) the syn-aldol adduct 4c in the presence of titanium tetrachloride. The stereocontrolled synthesis of (-)-pestalotin 7 has been achieved.

  DOI：

  10.1039/p19920000693

文献信息

• Electrochemical Deprotection of <i>para</i>-Methoxybenzyl Ethers in a Flow Electrolysis Cell
  作者：Robert A. Green、Katherine E. Jolley、Azzam A. M. Al-Hadedi、Derek Pletcher、David C. Harrowven、Oscar De Frutos、Carlos Mateos、David J. Klauber、Juan A. Rincón、Richard C. D. Brown

  DOI：10.1021/acs.orglett.7b00641

  日期：2017.4.21

  undivided electrochemical flow reactor in MeOH solution, leading to the unmasked alcohol and p-methoxybenzaldehyde dimethyl acetal as a byproduct. The electrochemical method removes the need for chemical oxidants, and added electrolyte (BF4NEt4) can be recovered and reused. The method was applied to 17 substrates with high conversions in a single pass, yields up to 92%, and up to 7.5 g h–1 productivity. The

  对-甲氧基苄基（PMB）醚的电化学脱保护是在未分开的电化学流动反应器中的MeOH溶液中进行的，从而产生未掩蔽的醇和对甲氧基苯甲醛二甲基乙缩醛的副产物。电化学方法消除了对化学氧化剂的需求，并且可以回收和再利用添加的电解质（BF 4 NEt 4）。该方法一次通过即可应用于高转化率的17种基材，产率高达92％，生产率高达7.5 gh –1。在一些其他常见的醇保护基的存在下，也选择性地除去了PMB保护基。
• AN ASYMMETRIC SYNTHESIS OF α-BENZYLOXY ALDEHYDES HAVING A CHIRAL TERTIARY CENTER—AN APPLICATION TO THE ASYMMETRIC SYNTHESIS OF<i>exo</i>-(+)-BREVICOMIN—
  作者：Masatoshi Asami、Teruaki Mukaiyama

  DOI：10.1246/cl.1983.93

  日期：1983.1.5

  α-Benzyloxy aldehydes having a chiral tertiary center at α-carbon atom are synthesized in high enantiomeric excess by successive treatment of 2-methoxycarbonyl-3-phenyl-1,3-diazabicyclo[3.3.0]octane with diisobutylaluminum hydride (DIBAL-H) and Grignard reagents. The asymmetric reaction is applied to the total synthesis of exo-(+)-brevicomin.

  通过用氢化二异丁基铝（DIBAL-H）和格氏试剂连续处理 2-甲氧基羰基-3-苯基-1,3-二氮杂双环[3.3.0]辛烷，合成出对映体过量的、在 α 碳原子上具有手性叔中心的 α-苄氧基醛。该不对称反应被用于外-(+)-brevicomin 的全合成。
• Concentration effects in chelation controlled reactions
  作者：James B. Springer、Julie DeBoardt、Robert C. Corcoran

  DOI：10.1016/0040-4039(95)01897-q

  日期：1995.11

  The diastereoselectivities of addition reactions of allyltrimethylsilane to an alpha-benzyloxyaldehyde were found to be relatively insensitive to the amount of added TiCl4, and to the absolute concentration of the 1:1 aldehyde/TiCl4 complex. In contrast, diastereoselectivities of similar additions to a structurally related beta-benzyloxyaldehyde were highly dependent on these variables.
• High diastereoselection in the aldol reaction of the bistrimethylsilyl enol ether of methyl acetoacetate with 2-benzyloxyhexanal: synthesis of (–)-pestalotin
  作者：Hisahiro Hagiwara、Katsuhiko Kimura、Hisashi Uda

  DOI：10.1039/p19920000693

  日期：——

  Aldol condensation of the bistrimethylsilyl enol ether of methyl acetoacetate, compound 2, with 2-benzyloxyhexanal 3c affords highly selectively (99:1) the syn-aldol adduct 4c in the presence of titanium tetrachloride. The stereocontrolled synthesis of (-)-pestalotin 7 has been achieved.
• An aldol - bislactonization route to α-methylene bis-γ-butyrolactones
  作者：Jittiwud Lertvorachon、Puttinan Meepowpan、Yodhathai Thebtaranonth

  DOI：10.1016/s0040-4020(98)00888-6

  日期：1998.11

  The syntheses of alpha-methylene gamma-butyrolactones and alpha-methylene bis-gamma-butyrolactones are made simple through the use of the versatile dimethyl itaconate - anthracene adduct, 1. (C) 1998 Elsevier Science Ltd. All rights reserved.