(R)-(-)-1-cyano-2-(1-naphthyloxy)ethyl acetate | 104760-42-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-(-)-1-cyano-2-(1-naphthyloxy)ethyl acetate
• 英文别名: (S)-(+)-1-cyano-2-(1-naphthyloxy)ethyl acetate；(S)-1-cyano-2-(naphthalen-1-yloxy)ethyl acetate；[(1S)-1-cyano-2-naphthalen-1-yloxyethyl] acetate
• CAS: 104760-42-1
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: XILYHAVZGBFXJI-ZDUSSCGKSA-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：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(-)-1-cyano-2-(1-naphthyloxy)ethyl acetate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 (S)-n-异丙基丙醇
  参考文献：
  名称：

  次要对映体回收：在β受体阻滞剂的对映选择性合成中的应用

  摘要：

  从手性醛的乙酰氰化获得的次要产物对映异构体的连续再循环提供了高度对映异构体富集的产物的获得。通过使用手性路易斯酸催化剂和生物催化剂的增强组合，以高对映体纯度形成在正常条件下以适中或较差的对映体比例获得的氰醇衍生物。通过两步程序，将最初获得的产物转化为β-肾上腺素能拮抗剂（S）-丙醇，（R）-二氯异丙基肾上腺素和（R）-nethalalol。

  DOI：

  10.1002/chem.201303890
• 作为产物：
  描述：

  2-萘-1-氧基乙醛 在 吡啶 、 hydroxynitrile lyase PcHNL₅ 作用下， 生成 (R)-(-)-1-cyano-2-(1-naphthyloxy)ethyl acetate
  参考文献：
  名称：

  一种用于将羟基腈裂解酶定向进化为氰醇合成的高通量筛选方法

  摘要：

  使生物氢氰化可测量：羟腈裂解酶 (HNL) 催化对映选择性裂解/形成氰醇。然而，目前确定氢氰化的方法不适合对这些生物催化剂的蛋白质工程进行突变体的大规模筛选。我们在此展示了一种用于氰醇合成的显色高通量筛选方法，该方法通过底物分析或 HNL 的定向进化进行验证。

  DOI：

  10.1002/cbic.202000658

文献信息

• One-Pot Synthesis of Optically Active Cyanohydrin Acetates from Aldehydes via Quinidine-Catalyzed Transhydrocyanation Coupled with Lipase-Catalyzed Kinetic Resolution in Organic Solvent
  作者：Minoru Inagaki、Akihiko Hatanaka、Mitsuo Mimura、Jun Hiratake、Takaaki Nishioka、Jun’ichi Oda

  DOI：10.1246/bcsj.65.111

  日期：1992.1

  transhydrocyanation allows for in situ racemization of the unreacted cyanohydrins and concurrent kinetic resolution by lipase enabled the preparation of (S)-3b–d with 40–82% e.e. in more than 50% yield. Polymer-supported cinchona alkaloid was also used as a catalyst for this one-pot reaction and showed the comparable chemical and optical yield to that for the soluble monomeric alkaloid. The insoluble polymer and lipase

  开发了一种新的一锅合成方法来制备旋光氰醇乙酸酯。通过奎尼丁催化的氢氰化反应从醛和丙酮氰醇中生成外消旋氰醇，然后使用乙酸异丙烯酯作为酰化剂，通过脂肪酶以立体选择性方式将所得氰醇 2a-j 乙酰化。多种醛 1a-j 成功地转化为相应的氰醇乙酸酯 3a-j，其 ee 为 47-95%，而没有分离不稳定的氰醇 2。此外，碱催化转移氢氰化的可逆性质允许未反应的氰醇原位外消旋化脂肪酶同时进行动力学拆分使 (S)-3b-d 能够以 50% 以上的产率制备 40-82% ee 的 (S)-3b-d。聚合物负载的金鸡纳生物碱也被用作这种一锅反应的催化剂，并显示出与可溶性单体生物碱相当的化学和光学产率。不溶性聚合物和脂肪酶...
• Lipase-catalyzed irreversible transesterification using enol esters: Resolution of cyanohydrins and syntheses of ethyl (R)-2-hydroxy-4-phenylbutyrate and (S)-propranolol
  作者：Yi-Fong Wang、Shui-Tein Chen、Kevin K.-C. Liu、Chi-Huey Wong

  DOI：10.1016/s0040-4039(00)99613-8

  日期：1989.1
• Ohta, Hiromichi; Miyamae, Yoshitaka; Tsuchihashi, Gen-ichi, Agricultural and Biological Chemistry, 1989, vol. 53, # 1, p. 215 - 222
  作者：Ohta, Hiromichi、Miyamae, Yoshitaka、Tsuchihashi, Gen-ichi

  DOI：——

  日期：——
• Preparation of optically active 1-acetoxy-2-aryloxypropionitriles and its application to a facile synthesis of (S)-(−)-propranolol
  作者：Noritada Matsuo、Nobuo Ohno

  DOI：10.1016/s0040-4039(01)80880-7

  日期：1985.1
• One-pot synthesis of optically active cyanohydrin acetates from aldehydes via lipase-catalyzed kinetic resolution coupled with in situ formation and racemization of cyanohydrins
  作者：Minoru Inagaki、Jun Hiratake、Takaaki Nishioka、Junichi Oda

  DOI：10.1021/jo00047a016

  日期：1992.10

  A novel one-pot synthesis of optically active cyanohydrin acetates from aldehydes has been accomplished by lipase-catalyzed kinetic resolution coupled with in situ formation and racemization of cyanohydrins in an organic solvent. Racemic cyanohydrins 2, generated from aldehydes 1 and acetone cyanohydrin in diisopropyl ether under the catalysis of basic anion-exchange resin (OH- form), were acetylated stereoselectively by a lipase from Pseudomonas cepacia (Amano) with isopropenyl acetate as an acylating reagent. The (S)-isomer of 2 was preferentially acetylated by the lipase, while the unreacted (R)-isomer was continuously racemized through reversible transhydrocyanation catalyzed by the resin. These processes thus enabled one-stage conversion of various aldehydes 1a-n into the corresponding (S)-cyanohydrin acetates 3a-n with up to 94% ee in 63-100% conversion yields. The racemization of the optically active cyanohydrin 2e by Amberlite IRA-904 (OH- form) was found to be much faster than the enzymatic acetylation, confirming the effective second-order asymmetric transformation. Enzymatic deacetylation of (S)-cyanohydrin acetates in an organic solvent and the synthesis of optically active pyrethroids are also described.