(4S)-3-[(3S,5S)-3,5-dimethyl-6-phenylmethoxyhexanoyl]-4-phenyl-1,3-oxazolidin-2-one | 306275-03-6

• 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: (4S)-3-[(3S,5S)-3,5-dimethyl-6-phenylmethoxyhexanoyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 306275-03-6
• 化学式: C₂₄H₂₉NO₄
• 分子量: 395.499
• InChiKey: NXVXLXPOSFCVLY-CNNODRBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-3-[(3S,5S)-3,5-dimethyl-6-phenylmethoxyhexanoyl]-4-phenyl-1,3-oxazolidin-2-one 在 palladium on activated charcoal 咪唑 、 manganese(IV) oxide 、 锂硼氢 、 甲酸 、 氢气 、 碘 、 二异丁基氢化铝 、 三乙基硼氢化锂 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 (E,6S,8R)-4,6,8-trimethyldec-4-en-1-yn-3-one
  参考文献：
  名称：

  Studies of novel cyclitols. A synthesis of 3′O,4′O-dimethylfuniculosin

  摘要：

  A synthesis of funiculosin dimethyl ether (2) is described. Methodologies for an asymmetric conjugate addition to establish the 1,3-anti dimethyl array, stereocontrolled formation of the Z,E-bis-allylic C-11 alcohol, and interception of a reactive pyridinone methide are examined. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01496-9
• 作为产物：
  描述：

  (2R)-3-bromo-2-[(methylpropyloxy)methyl]benzene 、 (4S)-N-crotonyl-4-phenyloxazolidin-2-one 在 copper(I) bromide dimethylsulfide complex 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到(4S)-3-[(3S,5S)-3,5-dimethyl-6-phenylmethoxyhexanoyl]-4-phenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Studies of novel cyclitols. A synthesis of 3′O,4′O-dimethylfuniculosin

  摘要：

  A synthesis of funiculosin dimethyl ether (2) is described. Methodologies for an asymmetric conjugate addition to establish the 1,3-anti dimethyl array, stereocontrolled formation of the Z,E-bis-allylic C-11 alcohol, and interception of a reactive pyridinone methide are examined. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01496-9

文献信息

• Efforts toward the Total Synthesis of (−)-Kendomycin
  作者：David R. Williams、Khalida Shamim

  DOI：10.1021/ol051512r

  日期：2005.9.1

  [structure: see text] The synthesis of an advanced component leading to (-)-kendomycin is described. The synthetic scheme features the application of asymmetric conjugate addition methodology for the early generation of the C13-C14 (E)-trisubstituted olefin, providing an efficient assembly of the ansa chain. Condensation reactions probe two strategies for attachment of the aromatic system.

  [结构：见正文]描述了导致（-）-kendomycin的高级组分的合成。该合成方案的特征在于不对称共轭加成方法在C13-C14（E）-三取代烯烃的早期生成中的应用，提供了ansa链的有效组装。缩合反应探讨了芳族体系连接的两种策略。
• Stereoselective synthesis of syn- and anti-1,3- and 1,2-dimethyl arrays via asymmetric conjugate additions
  作者：David R Williams、William S Kissel、Jie Jack Li、Richard J Mullins

  DOI：10.1016/s0040-4039(02)00638-x

  日期：2002.5

  Asymmetric conjugate additions have been investigated with enantiopure N-enoyloxazolidinones for efficient construction of syn and anti-1,3-dimethyl arrays on an acyclic carbon backbone. Reactions of Yamamoto organocopper species exhibit characteristics of double asymmetric induction resulting from influences of the 4-substituted chiral auxiliary and features of side chain stereochemistry.

  已经用对映体纯的N-烯酰恶唑烷酮研究了不对称共轭物的添加，以在无环碳主链上有效地构建顺式和反-1,3-二甲基阵列。山本有机铜物种的反应表现出由4-取代的手性助剂的影响和侧链立体化学的特征引起的双重不对称诱导的特征。
• Studies of novel cyclitols. A synthesis of 3′O,4′O-dimethylfuniculosin
  作者：David R Williams、Patrick D Lowder、Yu-Gui Gu

  DOI：10.1016/s0040-4039(00)01496-9

  日期：2000.12

  A synthesis of funiculosin dimethyl ether (2) is described. Methodologies for an asymmetric conjugate addition to establish the 1,3-anti dimethyl array, stereocontrolled formation of the Z,E-bis-allylic C-11 alcohol, and interception of a reactive pyridinone methide are examined. (C) 2000 Published by Elsevier Science Ltd.
• Construction of 4-Hydroxy-2-pyridinones. Total Synthesis of (+)-Sambutoxin
  作者：David R. Williams、Regis A. Turske

  DOI：10.1021/ol006410+

  日期：2000.10.1

  [GRAPHICS]Total synthesis of (+)-sambutoxin has been achieved, establishing the relative and absolute stereochemistry of the naturally occurring mycotoxin, Efforts feature methodology for enantiocontrolled construction of 1,3-anti dimethyl arrays and a novel Saegusa oxidation to provide a pyridinone methide leading to formation of the central dihydropyran ring.