(2R)-2-(1-naphthyl)methyl-1,3-propanediol-1-acetate | 128349-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R)-2-(1-naphthyl)methyl-1,3-propanediol-1-acetate
• 英文别名: (R)-3-Hydroxy-2-(1-naphthylmethyl)propyl acetate；[(2R)-2-(hydroxymethyl)-3-naphthalen-1-ylpropyl] acetate
• CAS: 128349-89-3
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: GZVLLFKMMIXVSY-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-2-(1-naphthyl)methyl-1,3-propanediol-1-acetate 在 吡啶 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 45.0h， 生成 (R)-3-Cyano-2-(1-naphthylmethyl)propyl acetate
  参考文献：
  名称：

  An efficient enantioselective total synthesis of antitumor lignans: synthesis of enantiomerically pure 4-hydroxyalkanenitriles via an enzymic reaction

  摘要：

  Efficient preparation of optically pure 4-hydroxyalkanenitriles, la-f, was achieved via an enzymatic reaction using lipase PS (Pseudomonas sp.). Optically pure (R)-4-hydroxy-3-[[3,4-(methylenedioxy)phenyl]methyl]butanenitrile (1a) was applied to the enantioselective synthesis of three types of antitumor lignans, (-)-hinokinin, (-)-isodeoxypodophyllotoxin, and (+)-isostegane.

  DOI：

  10.1021/jo00073a034
• 作为产物：
  描述：

  diethyl (1-naphthylmethyl)malonate 在 lithium aluminium tetrahydride 、 2,6-二叔丁基-4-甲基苯酚 作用下， 以 四氢呋喃 、 异丙醚 、 水 为溶剂， 反应 13.0h， 生成 (2R)-2-(1-naphthyl)methyl-1,3-propanediol-1-acetate
  参考文献：
  名称：

  An efficient enantioselective total synthesis of antitumor lignans: synthesis of enantiomerically pure 4-hydroxyalkanenitriles via an enzymic reaction

  摘要：

  Efficient preparation of optically pure 4-hydroxyalkanenitriles, la-f, was achieved via an enzymatic reaction using lipase PS (Pseudomonas sp.). Optically pure (R)-4-hydroxy-3-[[3,4-(methylenedioxy)phenyl]methyl]butanenitrile (1a) was applied to the enantioselective synthesis of three types of antitumor lignans, (-)-hinokinin, (-)-isodeoxypodophyllotoxin, and (+)-isostegane.

  DOI：

  10.1021/jo00073a034

文献信息

• Renin Inhibitors. II. Synthesis and Structure-Activity Relationships of N-Terminus Modified Inhibitors Containing a Homostatine Analogue.
  作者：Shugo ATSUUMI、Masato NAKANO、Yutaka KOIKE、Seiichi TANAKA、Hiroshi FUNABASHI、Kenji MATSUYAMA、Makiko NAKANO、Yoshio SAWASAKI、Kaoru FUNABASHI、Hajime MORISHIMA

  DOI：10.1248/cpb.40.3214

  日期：——

  The synthesis and structure-activity relationships of N-terminus modified renin inhibitors containing the homostatin analogue, (2RS,4S,5S)-5-amino-2-ethyl-4-hydroxy-7-methyloctanoic acid, are described. The compounds having a 3-alkyl (or aryl)sulfonylpropionyl residue at the N-terminus are found to be potent inhibitors which contain two amino acids. (2RS,4S,5S)-N-Isobutyl-5-[N-[(2S)-3-ethylsulfonyl-2-(1-

  描述了含有高抑素类似物（2RS，4S，5S）-5-氨基-2-乙基-4-羟基-7-甲基辛酸的N端修饰的肾素抑制剂的合成及其构效关系。发现在N-末端具有3-烷基（或芳基）磺酰基丙酰基残基的化合物是含有两个氨基酸的有效抑制剂。（2RS，4S，5S）-N-异丁基-5- [N-[（（2S）-3-乙基磺酰基] -2-（1-萘基甲基）丙酰基] -L-核糖基]-氨基-2-乙基-4-羟基-7-甲基辛酰胺（20）对人血浆肾素的IC50为0.5 nM，大鼠的口服生物利用度20为0.73％。分子建模研究中讨论了肾素与1和20的N末端之间的相互作用。
• Enzyme catalyzed resolution of alcohols using ethoxyvinyl acetate
  作者：Manfred Schudok、Gerhard Kretzschmar

  DOI：10.1016/s0040-4039(96)02333-7

  日期：1997.1

  1-Ethoxyvinyl acetate is an efficient irreversible acyl transfer reagent for lipase catalyzed esterification in organic solvents. The use of this reagent avoids reactive byproducts resulting in enzyme deactivation, in particular the formation of acetaldehyde using the widely employed vinyl acetate transesterification reagent. Copyright (C) 1996 Elsevier Science
• An efficient enantioselective preparation of 2-substituted-3-hydroxypropionic acids via chemo-enzymatic reaction
  作者：Shugo Atsuumi、Masato Nakano、Yutaka Koike、Seiichi Tanaka、Mitsuru Ohkubo、Toshiko Yonezawa、Hiroshi Funabashi、Junko Hashimoto、Hajime Morishima

  DOI：10.1016/0040-4039(90)80027-j

  日期：1990.1
• ATSUUMI, SHUGO;NAKANO, MASATO;KOIKE, YUTAKA;TANAKA, SEIICHI;OHKUBO, MITSU+, TETRAHEDRON LETT., 31,(1990) N1, C. 1601-1604
  作者：ATSUUMI, SHUGO、NAKANO, MASATO、KOIKE, YUTAKA、TANAKA, SEIICHI、OHKUBO, MITSU+

  DOI：——

  日期：——
• An efficient enantioselective total synthesis of antitumor lignans: synthesis of enantiomerically pure 4-hydroxyalkanenitriles via an enzymic reaction
  作者：Toshiyuki Itoh、Junichi Chika、Yumiko Takagi、Shigenori Nishiyama

  DOI：10.1021/jo00073a034

  日期：1993.10

  Efficient preparation of optically pure 4-hydroxyalkanenitriles, la-f, was achieved via an enzymatic reaction using lipase PS (Pseudomonas sp.). Optically pure (R)-4-hydroxy-3-[[3,4-(methylenedioxy)phenyl]methyl]butanenitrile (1a) was applied to the enantioselective synthesis of three types of antitumor lignans, (-)-hinokinin, (-)-isodeoxypodophyllotoxin, and (+)-isostegane.