(-)-(R)-5-(2-hydroxyethyl)-5-methyldihydrofuran-2-one | 127718-14-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (-)-(R)-5-(2-hydroxyethyl)-5-methyldihydrofuran-2-one
• 英文别名: 5-(2-hydroxyethyl)-5-methyldihydrofuran-2-one；(5R)-5-(2-hydroxyethyl)-5-methyloxolan-2-one
• CAS: 127718-14-3
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: WTHJXCAYUDGLJZ-SSDOTTSWSA-N

物化性质

• 沸点：
  288.1±13.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (-)-(R)-5-(2-hydroxyethyl)-5-methyldihydrofuran-2-one 在 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.33h， 生成 (R)-5-methyl-5-(4-methyl-2-oxopent-3-enyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  使用不对称多米诺烯丙基化反应的（+）-（R）-Pinnatolide的第一个对映选择性全合成。

  摘要：

  描述了（+）-（R）-Pinnatolide的有效全合成。作为关键步骤，使用乙酰丙酸甲酯的不对称多组分多烯丙基烯丙基化反应以高度选择性的方式形成季立构立体中心。

  DOI：

  10.1021/ol301932d
• 作为产物：
  描述：

  乙酰丙酸甲酯 在 三氟甲磺酸 、 palladium 10% on activated carbon 、 氢气 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， -78.0~45.0 ℃ 、8.0 MPa 条件下， 反应 28.25h， 生成 (-)-(R)-5-(2-hydroxyethyl)-5-methyldihydrofuran-2-one
  参考文献：
  名称：

  使用不对称多米诺烯丙基化反应的（+）-（R）-Pinnatolide的第一个对映选择性全合成。

  摘要：

  描述了（+）-（R）-Pinnatolide的有效全合成。作为关键步骤，使用乙酰丙酸甲酯的不对称多组分多烯丙基烯丙基化反应以高度选择性的方式形成季立构立体中心。

  DOI：

  10.1021/ol301932d

文献信息

• Total synthesis of (−)-betaenone C
  作者：Akitami Ichihara、Shokyo Miki、Hirokazu Kawagishi、Sadao Sakamura

  DOI：10.1016/s0040-4039(01)80742-5

  日期：1989.1

  Stereoselective synthesis of (−)-betaenone C through intramolecular Diels-Alder reaction has made possible to provide pertinent intermediates for the biosynthetic study of betaenones.

  通过分子内Diels-Alder反应的立体选择性合成（-）-β-烯酮C，有可能为β-烯酮的生物合成研究提供相关的中间体。
• New Bioorganic Reagents:  Evolved Cyclohexanone MonooxygenaseWhy Is It More Selective?
  作者：Margaret M. Kayser、Christopher M. Clouthier

  DOI：10.1021/jo061349t

  日期：2006.10.1

  Four mutants of the cyclohexanone monooxygenase (CHMO) evolved as catalysts for Baeyer-Villiger oxidation of 4-hydroxycyclohexanone were investigated as catalysts for a variety of 4-substituted and 4,4-disubstituted cyclohexanones. Several excellent catalytic matches (mutant/substrate) were identified. The most important, however, is the finding that, in a number of cases, a mutant with a single exchange, Phe432Ser, was shown to be as robust and more selective as a catalyst than the wild-type CHMO. All biotransformations were performed on a laboratory scale, allowing full characterization of the products. The absolute configurations of two products were established. A model suggesting a possible role of the 432 serine residue in enantioselectivity control is proposed.
• Increasing the enantioselectivity of cyclopentanone monooxygenase (CPMO): profile of new CPMO mutants
  作者：Christopher M. Clouthier、Margaret M. Kayser

  DOI：10.1016/j.tetasy.2006.10.001

  日期：2006.10

  A series of cyclohexanones substituted at the 4-position with a selection of hydrophobic and hydrophilic groups were used as substrates in the evaluation of six new cyclopentanone monooxygenase (CPMO) mutants. These mutants were obtained through evolutionary modifications in two specific regions of the CPMO's putative active site. Several mutant enzymes with improved enantioselectivity were identified. Analysis of the results, in terms of a diamond model, illustrates how a family of cyclohexanone substrates may be used to explore putative active sites of Baeyer-Villiger monooxygenases (BVMOs) and to design productive mutations for specific substrates. (c) 2006 Elsevier Ltd. All rights reserved.
• ICHIHARA, AKITAMI;MIKI, SHOKYO;KAWAGISHI, HIROKAZU;SAKAMURA, SADAO, TETRAHEDRON LETT., 30,(1989) N4, C. 4551-4554
  作者：ICHIHARA, AKITAMI、MIKI, SHOKYO、KAWAGISHI, HIROKAZU、SAKAMURA, SADAO

  DOI：——

  日期：——