(R)-3-(4-methoxybenzyloxy)-2-methylpropyl acetate | 374716-65-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-(4-methoxybenzyloxy)-2-methylpropyl acetate
• 英文别名: [(2R)-3-[(4-methoxyphenyl)methoxy]-2-methylpropyl] acetate
• CAS: 374716-65-1
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: HNNNLSAMQIRMHO-LLVKDONJSA-N

物化性质

• 沸点：
  345.8±27.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-(4-methoxybenzyloxy)-2-methylpropyl acetate 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 (R)-3-(4-methoxybenzyloxy)-2-methylpropanoic acid
  参考文献：
  名称：

  Nonanolide (Z)-Cytospolides D、E 及其立体异构体的化学酶促不对称全合成

  摘要：

  据报道，天然存在的癸内酯细胞质 D、E 和六种立体异构体的 (Z)-异构体的化学酶不对称全合成。该合成企业的主要亮点涉及适当官能化的酯化合物的闭环复分解 (RCM) 反应，该反应通过所需的酸和醇片段的 Yamaguchi 偶联组装而成。醇片段通过两种替代的化学酶促过程获得，一种是羟腈裂解酶介导的氢氰化，而脂肪酶催化的酯交换是第二种途径中的关键 sep。酸片段是通过前手性 2-甲基-1,3-丙二醇和 Corey-Bakshi-Shibata (CBS) 介导的立体选择性羰基还原的对映选择性酶解对称 (EED) 构建的。

  DOI：

  10.1002/ejoc.201301365
• 作为产物：
  描述：

  4-甲氧基溴苄 在 lipase from Candida rugosa 、 sodium hydride 作用下， 以 四氢呋喃 、 异丙醚 为溶剂， 反应 13.0h， 生成 (R)-3-(4-methoxybenzyloxy)-2-methylpropyl acetate
  参考文献：
  名称：

  Novel chiral lipoxygenase substrates: design and synthesis. Part 2

  摘要：

  A series of novel lipoxygenase substrates carrying a spacing modifier with a non-ionic hydroxyl terminus have been synthesized in an enantioselective fashion. One of the methylene hydrogens (flanked by the cis,cis-pentadienyl moiety) is replaced by alkyl, aryl and hydroxyl groups. The key steps in the synthesis involved enzymatic transesterification of 1,3-propanediol derivatives and two consecutive cis-selective Wittig olefinations. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00009-5

文献信息

• Chemoenzymatic Approach toward the Pure Enantiomers of 2-Methyl-1,3-propanediol Mono(p-Methoxybenzyl Ether)
  作者：Tomohiro Akeboshi、Yoshikazu Ohtsuka、Takashi Ishihara、Takeshi Sugai

  DOI：10.1002/1615-4169(200108)343:6/7<624::aid-adsc624>3.3.co;2-h

  日期：2001.8

  In a route towards the enantiomerically pure 2-methylpropane-1,3-diol mono(p-methoxybenzyl ether), which is an important starting material for natural product synthesis, a kinetic resolution approach by means of lipase-catalyzed hydrolysis as well as acylation has been elaborated. Candida antarctica lipase-catalyzed hydrolysis of the corresponding racemic acetate proceeded with high enantioselectivity (E 35). During the studies, a curious phenomenon was observed, namely, that the enantioselectivity gradually declined accompanying the progress of the hydrolysis. This was due to inhibition of the enzyme-catalyzed reaction caused by the accumulation of the resultant alcohol. The rate of reaction of the more reactive enantiomer became lower. This situation prompted a new process, which would minimize the contamination or the undesired enantiomer, prior to the enzyme-catalyzed hydrolysis. This was successfully achieved with the aid of another Pseudomonas cepacia lipase-catalyzed desymmetrization, taking advantage of the prochiral nature of the starting material, 2-methyl-1,3-propanediol, and the subsequent p-methoxybenzylation under mild conditions.
• Stereo flexible synthesis of the C8–C23 fragment of antarlides, androgen receptor antagonists
  作者：Palash Ghosh、Pralay Das、Prathama S. Mainkar、Thenkrishnan Kumaraguru、Rudrakshula Madhavachary、Srivari Chandrasekhar

  DOI：10.1039/d4ob00852a

  日期：——

  By combining enzymatic and chemical processes, we achieve stereo-flexible synthesis of a key C8–C23 fragment shared among all antarlides which are androgen receptor antagonists.