(3S)-1,3-dimethyl-3-(β-aminoethyl)-5-methoxyoxindole | 131101-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3S)-1,3-dimethyl-3-(β-aminoethyl)-5-methoxyoxindole
• 英文别名: (3S)-3-(2-aminoethyl)-5-methoxy-1,3-dimethylindol-2-one
• CAS: 131101-14-9
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: XEEBADQXIMNBQG-ZDUSSCGKSA-N

物化性质

• 沸点：
  456.0±45.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-1,3-dimethyl-3-(β-aminoethyl)-5-methoxyoxindole 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.83h， 生成 (3AS,8AR)-5-甲氧基-1,3A,8-三甲基-1,2,3,3A,8,8A-六氢吡咯并[2,3-B]吲哚
  参考文献：
  名称：

  Asymmetric alkylation of oxindoles: an approach to the total synthesis of (-)-physostigmine

  摘要：

  DOI：

  10.1021/jo00002a074
• 作为产物：
  描述：

  1,3-二甲基-5-甲氧基吲哚啉-2-酮 在 palladium on activated charcoal sodium tetrahydroborate 、 正丁基锂 、 ammonium formate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 正己烷 、 甲苯 为溶剂， 反应 6.5h， 生成 (3S)-1,3-dimethyl-3-(β-aminoethyl)-5-methoxyoxindole
  参考文献：
  名称：

  Enantioselective Creation of Quaternary Carbon Centers through Addition- Elimination Reaction: Asymmetric Nitroolefination of 3-Substituted 2-Oxindoles

  摘要：

  Nitroolefination of 3-substituted 2-oxindoles with nitroenamine (5) afforded the corresponding products having quaternary carbon centers with high ee in good yield. Application of this method to concise syntheses of (-)-esermethole (24) and (-)-pseudophrynaminol (28) is described.

  DOI：

  10.3987/com-97-s(n)107

文献信息

• Highly Enantioselective Intramolecular Cyanoamidation: (+)-Horsfiline, (−)-Coerulescine, and (−)-Esermethole
  作者：Venkata Jaganmohan Reddy、Christopher J. Douglas

  DOI：10.1021/ol902949d

  日期：2010.3.5

  octahydro-MonoPhos allowed the production of oxindoles with high enantioselectivities. Cyanoformamides bearing free N−H groups are now tolerated, potentially allowing protecting-group-free synthesis. Oxindole products of cyanoamidation are rapidly transformed into (+)-horsfiline, (−)-coerulescine, and (−)-esermethole.

  报道了具有合成上有用的对映选择性（ee高达99％）以生产3,3-二取代的羟吲哚的第一次不对称氰基酰胺化反应。具有手性亚磷酰胺配体的钯催化剂可激活氰基甲酰胺C-CN键，然后将其与束缚的链烯官能化，以生成全碳四元立体中心。八氢-MonoPhos的N，N-（i -Pr）2衍生物的使用允许生产具有高对映选择性的羟吲哚。现在可以耐受带有游离NH基的氰甲酰胺，潜在地允许无保护基的合成。氰基酰胺化的羟吲哚产物迅速转化为（+）-霍斯菲林，（-）-香兰素和（-）-乙二胺。
• Synthesis of (−)- and (+)-esermethole via chemical resolution of 1,3-dimethyl-3-(2-aminoethyl)-5-methoxyoxindole
  作者：Marco Pallavicini、Ermanno Valoti、Luigi Villa、Prancesca Lianza

  DOI：10.1016/s0957-4166(00)80490-5

  日期：1994.1

  A new synthesis of (-)- and (+)-esermethole (2 and 7 respectively), penultimate intermediates to (-)- and (+)-physostigmine, is described. Phase-transfer catalyzed dimethylation of 3-cyanomethyl -5-methoxyoxindole (3) and successive hydrogenation of the cyano group gave 1,3-dimethyl-3-(2-aminoethyl)-5-methoxyoxindole (5), which was efficiently resolved with optically active tartaric acids. Subsequent conversion to a carbamate and reductive cyclization performed by a standard method afforded both the enantiomers of esermethole. The enantiomeric excesses, determined by chiral HPLC analysis, were greater than 99.5%. In particular, analytical HPLC resolution of 5, previously reported as unfeasible, was achieved.
• LEE, THOMAS B. K.;WONG, GEORGE S. K., J. ORG. CHEM., 56,(1991) N, C. 872-875
  作者：LEE, THOMAS B. K.、WONG, GEORGE S. K.

  DOI：——

  日期：——
• Agents Useful for Reducing Amyloid Precursor Protein and Treating Dementia and Methods of Use Thereof
  申请人：Greig Nigel H.

  公开号：US20120295946A1

  公开（公告）日：2012-11-22

  The present invention provides compounds and methods of administering compounds to a subject that can reduce βAPP production and that is not toxic in a wide range of dosages. The present invention also provides non-carbamate compounds and methods of administering such compounds to a subject that can reduce βAPP production and that is not toxic in a wide range of dosages. It has been discovered that either the racemic or enantiomerically pure non-carbamate compounds can be used to decrease βAPP production.
• Enantioselective Creation of Quaternary Carbon Centers through Addition- Elimination Reaction: Asymmetric Nitroolefination of 3-Substituted 2-Oxindoles
  作者：Kaoru Fuji、Takeo Kawabata、Toshiumi Ohmori、Muhong Shang、Manabu Node

  DOI：10.3987/com-97-s(n)107

  日期：——

  Nitroolefination of 3-substituted 2-oxindoles with nitroenamine (5) afforded the corresponding products having quaternary carbon centers with high ee in good yield. Application of this method to concise syntheses of (-)-esermethole (24) and (-)-pseudophrynaminol (28) is described.