2,3-dihydro-6-phenyl-1,5-benzothiazepin-4(5H)-one | 1310699-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫氮卓类
• 英文名称: 2,3-dihydro-6-phenyl-1,5-benzothiazepin-4(5H)-one
• 英文别名: 2,3-dihydro-6-phenyl-1,5-benzo[b][1,4]thiazepine-4(5H)-one；6-phenyl-3,5-dihydro-2H-1,5-benzothiazepin-4-one
• CAS: 1310699-73-0
• 化学式: C₁₅H₁₃NOS
• 分子量: 255.34
• InChiKey: RLGFCMHXDPHPFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-6-phenyl-1,5-benzothiazepin-4(5H)-one 、 溴乙酸甲酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以76%的产率得到methyl (3,4-dihydro-4-oxo-6-phenyl-1,5-benzothiazepin-5(2H)-yl)acetate
  参考文献：
  名称：

  Isolation and Characterization of Atropisomers of Seven-Membered-Ring Benzolactams

  摘要：

  The atropisomeric properties of seven-membered-ring benzolactams (7a-c and 8a) [1,5-benzodiazepin-2-one (a), 1,5-benzothiazepin-4-one (b), and 1-benzazepin-2-one (c)] were examined. The atropisomers were isolated as the diastereomers with an (S)-phenethylamide moiety, which were characterized by X-ray crystallography, and the barriers to their interconversion were clarified.

  DOI：

  10.1021/jo2008725
• 作为产物：
  描述：

  2-氨基-3-氯苯硫酚 在 吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 21.5h， 生成 2,3-dihydro-6-phenyl-1,5-benzothiazepin-4(5H)-one
  参考文献：
  名称：

  Isolation and Characterization of Atropisomers of Seven-Membered-Ring Benzolactams

  摘要：

  The atropisomeric properties of seven-membered-ring benzolactams (7a-c and 8a) [1,5-benzodiazepin-2-one (a), 1,5-benzothiazepin-4-one (b), and 1-benzazepin-2-one (c)] were examined. The atropisomers were isolated as the diastereomers with an (S)-phenethylamide moiety, which were characterized by X-ray crystallography, and the barriers to their interconversion were clarified.

  DOI：

  10.1021/jo2008725

文献信息

• Active Conformation of Seven-Membered-Ring Benzolactams as New ACAT Inhibitors: Latent Chirality at N5 in the 1,5-Benzodiazepin-2-one Nucleus
  作者：Hidetsugu Tabata、Naoya Wada、Yuko Takada、Jun Nakagomi、Tomohiro Miike、Hiroaki Shirahase、Tetsuta Oshitari、Hideyo Takahashi、Hideaki Natsugari

  DOI：10.1002/chem.201103264

  日期：2012.2.6

  Nitrogen chirality: Potent new ACAT inhibitors with seven‐membered‐ring benzolactams as the core structures were first prepared, and the axial chirality recognized by the enzyme was clarified (e.g., 1; see scheme). The chirality at the axis (aS) of 1 controls the conformation of the entire lactam ring, causing the N5‐CH3 to arrange in a pseudo‐equatorial position (i.e., the amine at N5 is a chiral center

  氮手性：首先制备了以七元环苯并内酰胺为核心结构的强力新型ACAT抑制剂，并阐明了酶识别的轴向手性（例如1；参见方案）。轴（a S）为1的手性控制整个内酰胺环的构象，从而使N 5–CH 3排列在假赤道位置（即，N 5处的胺与S的手性中心‐配置）既处于晶体状态又处于溶液状态。
• Stereochemistry of 1,5-Benzothiazepin-4-one <i>S</i>-Oxide: Insight into the Stereogenic Elements at the Sulfur Atom and Axis
  作者：Hidetsugu Tabata、Tetsuya Yoneda、Tetsuta Oshitari、Hideyo Takahashi、Hideaki Natsugari

  DOI：10.1021/jo401020y

  日期：2013.6.21

  Oxidation of 1,5-benzothiazepin-4-one (5-A) stereoselectively afforded the S-oxide 8I-A (aS,1S) in preference to the diastereomer 8II-A (aS,1R) affected by the remote stereogenic axis. All the enantiomers (8I-A/8I-B and 8II-A/8II-B) were separated and isolated, and the interconversion between 8I and 8II (equilibrium ratio ≈5:1) was unequivocally verified to be caused by the rotation around the axis

  氧化1,5-苯并噻唑-4-（5 - A）立体选择性地提供了S-氧化物8I - A（a S，1 S），优先受非对映体8II - A（a S，1 R）影响。远程立体轴。分离并分离出所有对映体（8I - A / 8I - B和8II - A / 8II - B），以及8I和8II之间的相互转化。 （平衡比≈5：1）明确地证实是由围绕轴的旋转引起的。