1-(benzyloxy)octan-2-ol | 100011-00-5

• 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: 1-(benzyloxy)octan-2-ol
• 英文别名: 2-benzyloxy-1-octanol；1-phenylmethoxyoctan-2-ol
• CAS: 100011-00-5
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: OUMYUFFEOLOBDT-UHFFFAOYSA-N

物化性质

• 沸点：
  345.0±17.0 °C(Predicted)
• 密度：
  0.976±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(benzyloxy)octan-2-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以96%的产率得到1-(benzyloxy)octan-2-one
  参考文献：
  名称：

  Regio-selective hydroxylation of gem-difluorinated octanes by alkane hydroxylase (AlkB)

  摘要：

  gem-Difluoromethylene substituted molecules constitute a distinct class of fluorinated compounds. In this study, special chemistry has been developed for their preparation based on the highly selective terminal hydroxylation of these gem-difluorinated octanes by AlkB (alkane hydroxylase) from Pseudomonas putida Gpo1 to form gem-difluorinated octan-1-ols. The hydroxylation reaction is performed by whole-cell catalysis. Identification of the distal- and proximal-hydroxylation products was made by H-1, C-13, and F-19 NMR; GC and GC/MSD; and/or by comparison with authentic standards in GC. To the best of our knowledge, we have obtained the first synthesis of 2,2-, 3,3- and 4,4-difluorooctan-1-ols, from simple and inexpensive starting materials. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.101
• 作为产物：
  描述：

  1,2-辛二醇 、 溴甲苯 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以47%的产率得到1-(benzyloxy)octan-2-ol
  参考文献：
  名称：

  Regio-selective hydroxylation of gem-difluorinated octanes by alkane hydroxylase (AlkB)

  摘要：

  gem-Difluoromethylene substituted molecules constitute a distinct class of fluorinated compounds. In this study, special chemistry has been developed for their preparation based on the highly selective terminal hydroxylation of these gem-difluorinated octanes by AlkB (alkane hydroxylase) from Pseudomonas putida Gpo1 to form gem-difluorinated octan-1-ols. The hydroxylation reaction is performed by whole-cell catalysis. Identification of the distal- and proximal-hydroxylation products was made by H-1, C-13, and F-19 NMR; GC and GC/MSD; and/or by comparison with authentic standards in GC. To the best of our knowledge, we have obtained the first synthesis of 2,2-, 3,3- and 4,4-difluorooctan-1-ols, from simple and inexpensive starting materials. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.101

文献信息

• Reductive Cleavage of Acetals and Ketals with 9-Borabicyclo[3.3.1]nonane
  作者：John A. Soderquist、Iveliz Kock、Maria E. Estrella

  DOI：10.1021/op0601262

  日期：2006.9.1

  The reductive cleavage of benzaldehyde acetals and acetophenone ketals with the air-stable crystalline 9-borabicyclo[3.3.1]nonane dimer provides monobenzylated ether derivatives of diols and 1,2-oxygen-transposed β-phenethyl alcohols, respectively. The boron moiety is effectively recovered through simple procedures which involve convenient air-stable reagents and boron byproducts. The process is particularly

  苯甲醛缩醛和苯乙酮缩酮与空气稳定的结晶9-borabicyclo [3.3.1]壬烷二聚体的还原裂解分别提供了二醇和1,2-氧-转位的β-苯乙醇的单苄基醚衍生物。通过简单的方法有效地回收硼部分，该方法涉及方便的空气稳定试剂和硼副产物。该方法对于1，3-二醇是特别选择性的，仅给出更多取代的单苄基醚衍生物。用苯乙酮缩酮既发生还原又消除，使9-BBN-H氢硼化所得的苯乙烯，从而干净地生产1,2-氧转位的β-苯乙醇。该新方法的潜在应用已通过迷幻剂，甲斯卡林和止痛药布非那克的合成得到了说明。
• Chromium-Catalyzed Linear-Selective Alkylation of Aldehydes with Alkenes
  作者：Yuki Hirao、Yuri Katayama、Harunobu Mitsunuma、Motomu Kanai

  DOI：10.1021/acs.orglett.0c03180

  日期：2020.11.6

  We developed a chromium-catalyzed, photochemical, and linear-selective alkylation of aldehydes with alkylzirconium species generated in situ from a wide range of alkenes and Schwartz’s reagent. Photochemical homolysis of the C–Zr bond afforded alkyl radicals, which were then trapped by a chromium complex catalyst to generate the alkylchromium(III) species for polar addition to aldehydes. The reaction

  我们开发了铬催化，光化学和线性选择的醛醛烷基化反应，以及从各种烯烃和Schwartz试剂中就地生成的烷基锆物种。C-Zr键的光化学均质化提供了烷基，然后被铬络合物催化剂捕获，从而生成了烷基铬（III）物种，用于极性加成到醛中。反应在可见光照射下于环境温度下以高官能团耐受性进行。
• Highly regioselective ring opening of epoxides with alcohols catalyzed by organotin phosphate condensates
  作者：Junzo Otera、Yukari Yoshinaga、Kazuhisa Hirakawa、Tetsuya Nakata

  DOI：10.1016/s0040-4039(00)98156-5

  日期：1985.1

  Organotin phosphate condensates proved to catalyze the ring opening reaction of epoxides with alcohols in a highly regioselective manner.

  磷酸有机锡缩合物被证明以高度区域选择性的方式催化环氧化物与醇的开环反应。
• Novel Synthesis of Enol Ethers from β-Alkoxy Alcohols through<i>t</i>-BuOK-Promoted Elimination Reaction
  作者：Junzo Otera、Yoshihisa Niibo

  DOI：10.1246/bcsj.59.3977

  日期：1986.12

  A new synthesis of enol ethers from β-alkoxy alcohols was achieved through a t-BuOK-promoted elimination reaction.

  通过 t-BuOK 促进的消除反应，实现了从 β-烷氧基醇合成烯醇醚的新方法。
• Guindon, Yvan; Girard, Yves; Berthiaume, Sylvie, Canadian Journal of Chemistry, 1990, vol. 68, # 6, p. 897 - 902
  作者：Guindon, Yvan、Girard, Yves、Berthiaume, Sylvie、Gorys, Vida、Lemieux, Rene、Yoakim, Christiane

  DOI：——

  日期：——