(S)-5-tert-butylmorpholin-3-one | 180508-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (S)-5-tert-butylmorpholin-3-one
• 英文别名: (5S)-5-tert-butylmorpholin-3-one
• CAS: 180508-71-8
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: OVIYTRJLFBBCOX-ZCFIWIBFSA-N

物化性质

• 沸点：
  296.6±33.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-5-tert-butylmorpholin-3-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.33h， 以97%的产率得到(S)-3-叔丁基吗啉
  参考文献：
  名称：

  2-AMINOBENZOXAZOLE CARBOXAMIDES AS 5HT3 MODULATORS

  摘要：

  化学式I、II和III的化合物被披露为5-HT3受体拮抗剂。这些化合物在治疗化疗诱发恶心呕吐综合征（CINV）、腹泻型肠易激综合征（IBS-D）和其他疾病和症状中很有用。

  公开号：

  US20080255114A1
• 作为产物：
  描述：

  L-叔亮氨醇 、 氯乙酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 、 paraffin 为溶剂， 以69%的产率得到(S)-5-tert-butylmorpholin-3-one
  参考文献：
  名称：

  Alkylation Studies of N-Protected-5-substituted Morpholin-3-ones. A Stereoselective Approach to Novel Methylene Ether Dipeptide Isosteres

  摘要：

  We have developed a versatile new synthesis of the Psi[CH2O] pseudopeptides from N-protected-5-substituted morpholin-3-ones. The morpholin-3-ones are prepared in two steps from the corresponding amino alcohols by treatment with ethyl chloroacetate, followed by protection of the amide, We found that direct alkylation of the protected morpholin-3-ones gives the expected alkylation product where the electrophile approaches from the face opposite to the existing side chain (derived from the amino alcohol). If an S amino alcohol is used, this procedure results in the formation of the (SE) Psi[CH2O] dipeptide. Alternatively, the (S,S) Psi[CH2O] dipeptide can be obtained if the protected morpholin-3-one enolate is quenched with an aldehyde and the aldol product is dehydrated and reduced. We have explored an alkylation/deprotonation/kinetic protonation scheme which is also amenable to the preparation of (S,S) pseudodipetides. It is, of course, possible to obtain the corresponding (R,R) and (S,R) Psi[CH2O] dipeptides by simply selecting the appropriate amino alcohols and reaction conditions. Finally, we have established that this method is general and can be applied to the preparation of numerous Psi[CH2O] dipeptides which were previously unavailable by existing methods.

  DOI：

  10.1021/jo960496w

文献信息

• Stereoselective synthesis of novel methylene ether dipeptide isosteres
  作者：Bryan H. Norman、Julian S. Kroin

  DOI：10.1016/0040-4039(95)00712-l

  日期：1995.6

  We have developed a versatile new synthesis of the Ψ[CH2O] pseudopeptides from N-protected 5-substituted morpholin-3-ones. This approach focuses on a stereoselective alkylation of the morpholin-3-ones. The resulting alkylation products were used in the synthesis of some previously unavailable Ψ[CH2O] dipeptides.

  我们已经开发了一种由N保护的5-取代的吗啉-3-酮合成Ψ[CH 2 O]假肽的通用新方法。该方法集中于吗啉-3-酮的立体选择性烷基化。所得的烷基化产物用于合成某些先前无法获得的Ψ[CH 2 O]二肽。
• 2-aminobenzoxazole carboxamides as 5HT3 modulators
  申请人：Albany Molecular Research, Inc.

  公开号：US07863271B2

  公开（公告）日：2011-01-04

  Compounds of formulae I, II and III: are disclosed as 5-HT3 inhibitors. The compounds are useful in treating CINV, IBS-D and other diseases and conditions.

  公式I、II和III的化合物被披露为5-HT3抑制剂。这些化合物在治疗化疗诱导恶心和呕吐、腹泻型肠易激综合征和其他疾病和病况方面有用。
• US7863271B2
  申请人：——

  公开号：US7863271B2

  公开（公告）日：2011-01-04
• 2-AMINOBENZOXAZOLE CARBOXAMIDES AS 5HT3 MODULATORS
  申请人：Yang Zhicai

  公开号：US20080255114A1

  公开（公告）日：2008-10-16

  Compounds of formulae I, II and III: are disclosed as 5-HT3 inhibitors. The compounds are useful in treating CINV, IBS-D and other diseases and conditions.

  化学式I、II和III的化合物被披露为5-HT3受体拮抗剂。这些化合物在治疗化疗诱发恶心呕吐综合征（CINV）、腹泻型肠易激综合征（IBS-D）和其他疾病和症状中很有用。
• Alkylation Studies of <i>N</i>-Protected-5-substituted Morpholin-3-ones. A Stereoselective Approach to Novel Methylene Ether Dipeptide Isosteres
  作者：Bryan H. Norman、Julian S. Kroin

  DOI：10.1021/jo960496w

  日期：1996.1.1

  We have developed a versatile new synthesis of the Psi[CH2O] pseudopeptides from N-protected-5-substituted morpholin-3-ones. The morpholin-3-ones are prepared in two steps from the corresponding amino alcohols by treatment with ethyl chloroacetate, followed by protection of the amide, We found that direct alkylation of the protected morpholin-3-ones gives the expected alkylation product where the electrophile approaches from the face opposite to the existing side chain (derived from the amino alcohol). If an S amino alcohol is used, this procedure results in the formation of the (SE) Psi[CH2O] dipeptide. Alternatively, the (S,S) Psi[CH2O] dipeptide can be obtained if the protected morpholin-3-one enolate is quenched with an aldehyde and the aldol product is dehydrated and reduced. We have explored an alkylation/deprotonation/kinetic protonation scheme which is also amenable to the preparation of (S,S) pseudodipetides. It is, of course, possible to obtain the corresponding (R,R) and (S,R) Psi[CH2O] dipeptides by simply selecting the appropriate amino alcohols and reaction conditions. Finally, we have established that this method is general and can be applied to the preparation of numerous Psi[CH2O] dipeptides which were previously unavailable by existing methods.