cis-(+/-)-2,3-dihydro-3-hydroxy-2-phenyl-1,5-benzothiazepin-4(5H)-one | 27068-82-2

• 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: cis-(+/-)-2,3-dihydro-3-hydroxy-2-phenyl-1,5-benzothiazepin-4(5H)-one
• 英文别名: 3c-hydroxy-2r-phenyl-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one；(2R,3R)-3-hydroxy-2-phenyl-3,5-dihydro-2H-1,5-benzothiazepin-4-one
• CAS: 27068-82-2；30825-33-3；94098-32-5；137940-11-5；137940-12-6；137940-13-7；137940-14-8
• 化学式: C₁₅H₁₃NO₂S
• 分子量: 271.34
• InChiKey: ZUOHMTWRFCETKE-UONOGXRCSA-N

物化性质

• 沸点：
  516.9±50.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 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：
  74.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-(+/-)-2,3-dihydro-3-hydroxy-2-phenyl-1,5-benzothiazepin-4(5H)-one 、 碘甲烷 生成 3c-hydroxy-5-methyl-2r-phenyl-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one
  参考文献：
  名称：

  Kugita,H. et al., Chemical and pharmaceutical bulletin, 1970, vol. 18, p. 2284 - 2289

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl (2R,3R)-3-(2-aminophenyl)sulfanyl-2-hydroxy-3-phenylpropanoate 生成 cis-(+/-)-2,3-dihydro-3-hydroxy-2-phenyl-1,5-benzothiazepin-4(5H)-one
  参考文献：
  名称：

  HASHIYAMA, TOMIKI;INOUE, HIROZUMI;KONDA, MIKIHIKO;TAKEDA, MIKIO, CHEM. AND PHARM. BULL., 1985, 33, N 3, 1256-1259

  摘要：

  DOI：

文献信息

• Stereoselective addition of 2-aminothiophenol to α-alkoxycinnamic acid derivatives—alternative synthesis of (±)-diltiazem—
  作者：Okiko Miyata、Tetsuro Shinada、Takeaki Naito、Ichiya Ninomiya、Tadamasa Date、Kimio Okamura

  DOI：10.1016/s0040-4020(01)88031-5

  日期：1993.9

  A stereocontrolled synthesis of (±)-diltiazem by applying nucleophilic addition of 2-aminothiophenol to α-alkoxycinnamic acid derivatives is described.

  描述了通过将2-氨基硫酚亲核加成到α-烷氧基肉桂酸衍生物上的（±）-地尔硫m的立体控制合成。
• Process for preparing optically active benzothiazepine compounds by asymmetric reduction
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：EP0551076A1

  公开（公告）日：1993-07-14

  Process for preparing optically active cis-3-hydroxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one compounds [I] of the formula: wherein Ring A and Ring B are substituted or unsubstituted benzene, R¹ is hydrogen or di-lower alkylaminoalkyl, which comprises subjecting 1,5-benzothiazepin-4(5H)-one (II) of the formula [II]: wherein R⁴ is hydrogen or lower alkanoyl, and the other symbols are the same as defined above, to asymmetric reduction with a reaction product of optically active α-amino acid and metal hydride, in high optically yield, and said compounds [I] are very important as intermediate for preparing various medicines.

  制备光学活性顺式-3-羟基-2,3-二氢-1,5-苯并硫氮杂卓-4(5H)-酮化合物[I]的工艺： 其中环 A 和环 B 是取代或未取代的苯，R¹ 是氢或二低级烷基氨基烷基，该工艺包括将式[II]的 1，5-苯并硫氮杂卓-4(5H)-酮(II)： 其中 R⁴为氢或低级烷酰基，其他符号与上述定义相同，用光学活性 α-氨基酸和金属氢化物的反应产物进行不对称还原，光学收率高，所述化合物[I]是制备各种药物的非常重要的中间体。
• Process for preparing optically active benzothiazepine compound, and intermediate therefor
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：EP0826678A1

  公开（公告）日：1998-03-04

  Powdery aggregate of 2-phenyl-1,5-benzothiazepin-3,4(2H,5H)-dione compound: wherein Ring A and Ring B are benzene ring having optionally substituent selected from lower alkyl, lower alkoxy and halogen, which is prepared by admixing solution of the compound (II) in polar organic solvent with solvent which does not substantially dissolve the compound (II) but is miscible with said polar organic solvent, and separating and collecting the resultant particles of the compound (II). Said aggregate of the compound (II) can be converted into optically active 3-hydroxy-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one compounds (I) on industrial scale, which are useful as intermediate for various medicaments.

  2-苯基-1,5-苯并硫氮杂卓-3,4(2H,5H)-二酮化合物的粉末状集合体： 将化合物(II)在极性有机溶剂中的溶液与基本上不溶解化合物(II)但能与所述极性有机溶剂混溶的溶剂混合，并分离和收集所得到的化合物(II)颗粒。上述化合物（II）的集合体可在工业规模上转化为具有光学活性的 3-羟基-2-苯基-2,3-二氢-1,5-苯并硫氮杂卓-4(5H)-酮化合物（I），这些化合物可用作各种药物的中间体。
• Hashiyama, Tomiki; Inoue, Hirozumi; Konda, Mikihiko, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 3, p. 1256 - 1259
  作者：Hashiyama, Tomiki、Inoue, Hirozumi、Konda, Mikihiko、Takeda, Mikio

  DOI：——

  日期：——
• Hashiyama, Tomiki; Inoue, Hirozumi; Konda, Mikihiko, Journal of the Chemical Society. Perkin transactions I, 1984, # 8, p. 1725 - 1732
  作者：Hashiyama, Tomiki、Inoue, Hirozumi、Konda, Mikihiko、Takeda, Mikio

  DOI：——

  日期：——