(3S,5R)-3-methyl-5-(phenylmethoxymethyl)oxolan-2-one | 116060-83-4

• 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: (3S,5R)-3-methyl-5-(phenylmethoxymethyl)oxolan-2-one
• CAS: 116060-83-4
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: GBGPWVYIQOHUSE-CMPLNLGQSA-N

物化性质

• 沸点：
  357.3±15.0 °C(predicted)
• 密度：
  1.096±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (3S,5R)-3-methyl-5-(phenylmethoxymethyl)oxolan-2-one 在 正丁基锂 作用下， 生成 (3S,5R)-1-dimethoxyphosphoryl-3-methyl-6-phenylmethoxy-5-triethylsilyloxyhexan-2-one
  参考文献：
  名称：

  Lituarine合成研究。有效的，立体控制的常见的c（7-19）三环spiroketal片段的构造。

  摘要：

  一个高效，立体控制的合成（+）-4，共同的C（7-19）三环螺环链片段的A，B和C（1-3），。合成的重点包括访问C（8-12）吡喃环的一个非常容易的6-内环化和动力学控制酸催化的螺缩酮化。[反应：看文字]

  DOI：

  10.1021/ol016948v
• 作为产物：
  描述：

  (R)-苄氧甲基环氧乙烷 在 硫酸 、 (R)-苄氧甲基环氧乙烷 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.5h， 生成 (3S,5R)-3-methyl-5-(phenylmethoxymethyl)oxolan-2-one
  参考文献：
  名称：

  Practical Syntheses of Enantiomerically Enriched γ-Lactones and γ-Hydroxy Ketones by the Alkylation of Pseudoephedrine Amides with Epoxides and Their Derivatives

  摘要：

  Pseudoephedrine amide enolates are shown to undergo efficient alkylation reactions with epoxides as electrophiles. Reactions with monosubstituted epoxides are subject to stereochemical matching such that the pairing leading to the 1,3-syn diastereomer is a highly selective, synthetically useful process, while the pairing forming the 1,3-anti diastereomer is not. Reactions with the 1,1-disubstituted epoxide isobutylene oxide are also highly diastereoselective and synthetically useful, but ethylene oxide exhibits poor diastereoselectivity. As an alternative to the use of ethylene oxide, 2-(tert-butyldimethylsilyloxy)ethyl iodide is shown to undergo highly diastereoselective and efficient alkylation reactions with pseudoephedrine amide enolates. Interestingly, epoxides and alkyl halides are found to attack opposite pi-faces of pseudoephedrine amide enolates. The products of each of these alkylation reactions are transformed efficiently into gamma-lactones by acidic hydrolysis and into methyl ketones by the addition of methyllithium. The methodology described provides useful procedures for the synthesis of enantiomerically enriched gamma-lactones and gamma-hydroxy ketones.

  DOI：

  10.1021/jo952032o

文献信息

• Total Syntheses of the Assigned Structures of Lituarines B and C
  作者：Amos B. Smith、Matthew O. Duffey、Kallol Basu、Shawn P. Walsh、Hans W. Suennemann、Michael Frohn

  DOI：10.1021/ja078293k

  日期：2008.1.1

  The first syntheses of the structures assigned to the marine natural products lituarines B and C have been achieved via a highly convergent sequence. The structures comprise complex, highly oxygenated 25-membered macrolactones possessing a rare tricyclic spiroketal and a unique (E,Z)-dienamide side chain. Unfortunately, the spectral properties of the synthetic compounds did not match those reported

  分配给海洋天然产物 lituarines B 和 C 的结构的首次合成是通过高度收敛的序列实现的。该结构包括复杂的、高度氧化的 25 元大环内酯，具有罕见的三环螺缩酮和独特的 (E,Z)-二烯酰胺侧链。不幸的是，合成化合物的光谱特性与天然 lituarines 的光谱特性不匹配。本通讯提供了 lituarines B 和 C 指定结构的全合成，以及支持结构指定的证据。
• TAKANO SEIICHI; KUDO JUNKO; TAKAHASHI MICHIYASU; OGASAWARA KUNIO, TETRAHEDRON LETT., 27,(1986) N 21, 2405-2408
  作者：TAKANO SEIICHI、 KUDO JUNKO、 TAKAHASHI MICHIYASU、 OGASAWARA KUNIO

  DOI：——

  日期：——
• Practical Syntheses of Enantiomerically Enriched γ-Lactones and γ-Hydroxy Ketones by the Alkylation of Pseudoephedrine Amides with Epoxides and Their Derivatives
  作者：Andrew G. Myers、Lydia McKinstry

  DOI：10.1021/jo952032o

  日期：1996.1.1

  Pseudoephedrine amide enolates are shown to undergo efficient alkylation reactions with epoxides as electrophiles. Reactions with monosubstituted epoxides are subject to stereochemical matching such that the pairing leading to the 1,3-syn diastereomer is a highly selective, synthetically useful process, while the pairing forming the 1,3-anti diastereomer is not. Reactions with the 1,1-disubstituted epoxide isobutylene oxide are also highly diastereoselective and synthetically useful, but ethylene oxide exhibits poor diastereoselectivity. As an alternative to the use of ethylene oxide, 2-(tert-butyldimethylsilyloxy)ethyl iodide is shown to undergo highly diastereoselective and efficient alkylation reactions with pseudoephedrine amide enolates. Interestingly, epoxides and alkyl halides are found to attack opposite pi-faces of pseudoephedrine amide enolates. The products of each of these alkylation reactions are transformed efficiently into gamma-lactones by acidic hydrolysis and into methyl ketones by the addition of methyllithium. The methodology described provides useful procedures for the synthesis of enantiomerically enriched gamma-lactones and gamma-hydroxy ketones.
• Lituarine Synthetic Studies. An Efficient, Stereocontrolled Construction of the Common C(7−19) Tricyclic Spiroketal Fragment
  作者：Amos B. Smith、Michael Frohn

  DOI：10.1021/ol016948v

  日期：2001.11.1

  A highly efficient, stereocontrolled synthesis of (+)-4, the common C(7-19) tricyclic spiroketal fragment of the lituarines A, B, and C (1-3), has been achieved. Highlights of the synthesis include a remarkably facile 6-endo cyclization to access the C(8-12) pyran ring and a kinetically controlled acid-catalyzed spiroketalization. [reaction: see text]

  一个高效，立体控制的合成（+）-4，共同的C（7-19）三环螺环链片段的A，B和C（1-3），。合成的重点包括访问C（8-12）吡喃环的一个非常容易的6-内环化和动力学控制酸催化的螺缩酮化。[反应：看文字]