1-乙酰氧基-2-(6-甲氧基-2-萘基)丙烷 | 76842-29-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-乙酰氧基-2-(6-甲氧基-2-萘基)丙烷
• 英文名称: 2-(6-methoxynaphthalen-2-yl)propyl acetate
• 英文别名: 1-acetoxy-2-(6-methoxy-2-naphthyl)propane
• CAS: 76842-29-0
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: AEEKXZJYJVMYAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-乙酰氧基-2-(6-甲氧基-2-萘基)丙烷 在 重铬酸吡啶 、 phosphate buffer 、 pig pancreatic lipase 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 72.0h， 生成 萘普生
  参考文献：
  名称：

  Chemoenzymatic synthesis of antiinflammatory drugs in enantiomerically pure form

  摘要：

  A novel chemoenzymatic route to chiral anti-inflammatory drugs in enantiomerically pure form is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00184-1
• 作为产物：
  描述：

  萘普生甲基酯 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 1-乙酰氧基-2-(6-甲氧基-2-萘基)丙烷
  参考文献：
  名称：

  Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates

  摘要：

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.009

文献信息

• Iron‐Catalysed Remote C(sp ³ )−H Azidation of <i>O</i> ‐Acyl Oximes and <i>N</i> ‐Acyloxy Imidates Enabled by 1,5‐Hydrogen Atom Transfer of Iminyl and Imidate Radicals: Synthesis of γ‐Azido Ketones and β‐Azido Alcohols
  作者：Rubén O. Torres‐Ochoa、Alexandre Leclair、Qian Wang、Jieping Zhu

  DOI：10.1002/chem.201901079

  日期：2019.7.17

  acetylacetonate [Fe(acac)3], the reaction of structurally diverse ketoxime esters with trimethylsilyl azide (TMSN3) afforded γ‐azido ketones in good to excellent yields. This unprecedented distal γ‐C(sp3)−H bond azidation reaction went through a sequence of reductive generation of an iminyl radical, 1,5‐hydrogen atom transfer (1,5‐HAT) and iron‐mediated redox azido transfer to the translocated carbon radical

  在催化量的乙酰丙酮铁（III）[Fe（acac）3 ]的存在下，结构多样的酮肟酸酯与三甲基硅烷基叠氮化物（TMSN 3）的反应可提供良好产率的γ-叠氮基酮。前所未有的远端γ-C（sp 3）-H键叠氮化反应经历了亚胺基的还原生成，1,5-氢原子转移（1,5-HAT）以及铁介导的氧化还原叠氮基转移至易位的碳自由基。TMSN 3不仅用作功能化未激活的C（sp 3）-H键的氮源，而且还用作还原剂以原位生成催化活性的Fe II。基于相同的原理，一种新颖的β-C（sp3）-H通过N-酰氧基酰亚胺的醇官能化随后被实现，在将所得的酯水解后，导致β-叠氮基醇，这是有机和药物化学的重要组成部分。
• Process for the enzymatic separation of the optical isomers of racemic alpha-alkyl-substituted primary alcohols
  申请人：ISTITUTO GUIDO DONEGANI S.p.A.

  公开号：EP0328125A2

  公开（公告）日：1989-08-16

  A process is disclosed for the biotechnological resolution by means of enzymatic transesterification of the relevant racemic mixture of the optical isomers of α-alkyl-substituted alcohols having the formula (I): wherein: R represents a linear or branched (C₁-C₂₀)-alkyl or alkenyl group or an aryl group, also substituted or condensed with other groups, in parti­cular a group of formula (II) or (III): wherein: Rii represents a (C₁-C₈)-alkyl group, a (C₁-C₄)-alkenyl group, an alkoxy, phenyl, phenoxy, benzoyl, heterocyclic group; Riii represents a hydrogen or halogen atom; Riv represents a (C₁-C₄)-alkyl group, and wherein Ri represents a (C₁-C₄)-alkyl group either equal to, or different from, R, in the presence of an enzyme either free or immobilized on a support capable of selectively causing the S isomer to be esterified, with the R isomer being left substantially unchanged, and said isomers are then separated according to techniques known from the prior art. The process is used in the synthesis of anti-­inflammatory agents.

  本发明公开了一种通过酶促酯交换反应，以生物技术解决具有式 (I) 的 α-烷基取代醇的光学异构体的相关外消旋混合物的工艺： 其中 R 代表线性或支链（C₁-C₂₀）烷基或烯基或芳基，也可与其他基团，特别是式 (II) 或 (III) 基团取代或缩合： 其中 Rii 代表(C₁-C₈)-烷基、(C₁-C₄)-烯基、烷氧基、苯基、苯氧基、苯甲酰基、杂环基； Riii 代表氢原子或卤素原子； Riv 代表 (C₁-C₄)- 烷基、 其中 Ri 代表与 R 相同或不同的 (C₁-C₄)- 烷基、 在一种酶的存在下，该酶可以是游离的，也可以是固定在支持物上的，该酶能够选择性地使 S 异构体酯化，而 R 异构体基本保持不变，然后根据现有技术中已知的技术分离所述异构体。 该工艺可用于合成抗炎剂。
• DEL, BONO, R.
  作者：DEL, BONO, R.

  DOI：——

  日期：——
• Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates
  作者：Surrinder Koul、Jawahir Lal Koul、Budh Singh、Munish Kapoor、Rajinder Parshad、Kuldeep S. Manhas、Subhash C. Taneja、Ghulam N. Qazi

  DOI：10.1016/j.tetasy.2005.07.009

  日期：2005.8

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.
• Chemoenzymatic synthesis of antiinflammatory drugs in enantiomerically pure form
  作者：Amit Basak、Ahindra Nag、Gautam Bhattacharya、Subrata Mandal、Sikha Nag

  DOI：10.1016/s0957-4166(00)00184-1

  日期：2000.6

  A novel chemoenzymatic route to chiral anti-inflammatory drugs in enantiomerically pure form is described. (C) 2000 Elsevier Science Ltd. All rights reserved.