3-hydroxyundecanenitrile | 40165-83-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxyundecanenitrile
• CAS: 40165-83-1
• 化学式: C₁₁H₂₁NO
• 分子量: 183.294
• InChiKey: SMKQDVZYJFWMPD-UHFFFAOYSA-N

物化性质

• 沸点：
  318.5±15.0 °C(Predicted)
• 密度：
  0.910±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 3-hydroxyundecanenitrile 以 吡啶 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 Acetic acid 1-cyanomethyl-nonyl ester
  参考文献：
  名称：

  Thiacrown Ether Technology in Lipase-Catalyzed Reaction:  Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis

  摘要：

  Both reaction rate and enantioselectivity in Pseudomonas cepacia lipase (PCL)-catalyzed hydrolysis of 3-hydroxyalkanenitrile acetates were significantly changed by the addition of catalytic amounts of thiacrown ether (1,4,8,11-tetrathiacyclotetradecane). Although the-reaction rate of various nitriles was accelerated, the enantioselectivity greatly depended on the nature of the substrate. Among 10 substrates tested, thiacrown ether offered highest enantioselectivity in PCL-catalyzed hydrolysis of 1-(cyanomethyl)propyl acetate. Forty or more times this crown ether, molarity based on the enzyme, was required to attain an acceptably high reaction rate and enantioselectivity. Applying this technology, we succeeded in synthesizing the optically pure attractant pheromone of ant Myrmica scabrinodis (A), (R)-3-octanol and its antipode of (S)-isomer in good overall yields.

  DOI：

  10.1021/jo971288m
• 作为产物：
  描述：

  1,2-二甲基丁炔酯 、 氰化钠 在 氯化铵 作用下， 以 甲醇 、 水 为溶剂， 反应 15.0h， 以81%的产率得到3-hydroxyundecanenitrile
  参考文献：
  名称：

  Efficient Lipase-Catalyzed Kinetic Resolution and Dynamic Kinetic Resolution of β-Hydroxy Nitriles. A Route to Useful Precursors for γ-Amino Alcohols

  摘要：

  DOI：

  10.1002/1615-4169(200108)343:6/7<726::aid-adsc726>3.3.co;2-5

文献信息

• Catalytic cyanomethylation of carbonyl compounds and imines with highly basic phosphine
  作者：Satoru Matsukawa、Eri Kitazaki

  DOI：10.1016/j.tetlet.2008.02.155

  日期：2008.4

  A highly basic phosphine, tris(2,4,6-trimethoxy phenyl)phosphine (TTMPP), catalyzes cyanomethylation using trimethylsilylacetonitrile (TMSCH2CN) to give the corresponding products in good to high yields, with both carbonyl compounds and imines.

  高碱性膦三（2,4,6-三甲氧基苯基）膦（TTMPP）使用三甲基甲硅烷基乙腈（TMSCH 2 CN）催化氰基甲基化，从而以羰基化合物和亚胺的高收率得到相应的产物。
• Method of manufacturing cyano compounds
  申请人：Shibasaki Masakatsu

  公开号：US20050004388A1

  公开（公告）日：2005-01-06

  A method of manufacturing a cyano compound by reacting a carbonyl compound with a nitrile compound having at least one α-hydrogen atom in the presence of a ligand and a metal compound of formula (III), MX  (III) wherein M is a copper atom or a silver atom, and X is an alkoxy group, an alkyl group, an aryl group or an anionic residue.

  通过在配体和化合物的存在下，将羰基化合物与至少含有一个α-氢原子的腈化合物反应，制备氰基化合物的方法，其中化合物的公式为（III），MX，其中M是铜原子或银原子，X是烷氧基团、烷基团、芳基团或阴离子残基。
• Efficient Lipase-Catalyzed Kinetic Resolution and Dynamic Kinetic Resolution of β-Hydroxy Nitriles. Correction of Absolute Configuration and Transformation to Chiral β-Hydroxy Acids and γ-Amino Alcohols
  作者：Oscar Pàmies、Jan-E. Bäckvall

  DOI：10.1002/1615-4169(200210)344:9<947::aid-adsc947>3.0.co;2-z

  日期：2002.10

  Chemoenzymatic dynamic kinetic resolution of β-hydroxy nitriles 1 has been carried out using Candida antarctica lipase B and a ruthenium catalyst. The use of a hydrogen source to depress ketone formation in the dynamic kinetic resolution yields the corresponding acetates 2 in good yield and high enantioselectivity. It is shown that the ruthenium catalyst and the enzyme can be recycled when used in

  β-羟基腈1的化学酶动力学动力学拆分已使用南极假丝酵母脂肪酶B和钌催化剂进行。使用氢源以动态动力学拆分抑制酮的形成以良好的产率和高的对映选择性产生相应的乙酸酯2。结果表明，钌催化剂和酶在单独的反应中使用时可以循环使用。我们还报告了从1和2制备各种对映体纯的β-羟基酸衍生物和γ-氨基醇的情况。后一化合物也用于建立1和2的正确绝对构型。
• US7355061B2
  申请人：——

  公开号：US7355061B2

  公开（公告）日：2008-04-08
• Thiacrown Ether Technology in Lipase-Catalyzed Reaction:  Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis
  作者：Toshiyuki Itoh、Koichi Mitsukura、Wipa Kanphai、Yumiko Takagi、Hiroshi Kihara、Hiroshi Tsukube

  DOI：10.1021/jo971288m

  日期：1997.12.1

  Both reaction rate and enantioselectivity in Pseudomonas cepacia lipase (PCL)-catalyzed hydrolysis of 3-hydroxyalkanenitrile acetates were significantly changed by the addition of catalytic amounts of thiacrown ether (1,4,8,11-tetrathiacyclotetradecane). Although the-reaction rate of various nitriles was accelerated, the enantioselectivity greatly depended on the nature of the substrate. Among 10 substrates tested, thiacrown ether offered highest enantioselectivity in PCL-catalyzed hydrolysis of 1-(cyanomethyl)propyl acetate. Forty or more times this crown ether, molarity based on the enzyme, was required to attain an acceptably high reaction rate and enantioselectivity. Applying this technology, we succeeded in synthesizing the optically pure attractant pheromone of ant Myrmica scabrinodis (A), (R)-3-octanol and its antipode of (S)-isomer in good overall yields.