cis-2-(dimethylamino)-2,3-dihydroinden-1-ol | 23337-86-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: cis-2-(dimethylamino)-2,3-dihydroinden-1-ol
• 英文别名: cis-2-N,N-Dimethylamino-1-indanol；(1S,2R)-2-(dimethylamino)-2,3-dihydro-1H-inden-1-ol
• CAS: 23337-86-2；23359-90-2；64244-93-5；64244-94-6；71798-47-5
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: JEENINFBIUDYBJ-MNOVXSKESA-N

物化性质

• 沸点：
  299.5±40.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-2-(dimethylamino)-2,3-dihydroinden-1-ol 、 苯酚 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 以59%的产率得到trans-N,N-dimethyl-2,3-dihydro-1-phenoxyinden-2-amine oxalate
  参考文献：
  名称：

  The Mitsunobu reaction of some indan amino alcohols

  摘要：

  The Mitsunobu reaction, utilizing several phenols, has been applied to a series of indan amino alcohols. An interesting example of configurational retention as a result of an aziridinium intermediate was discovered.

  DOI：

  10.1021/jo00002a033
• 作为产物：
  描述：

  2-(dimethylamino)-2,3-dihydroinden-1-one hydrochloride 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以90%的产率得到cis-2-(dimethylamino)-2,3-dihydroinden-1-ol
  参考文献：
  名称：

  The Mitsunobu reaction of some indan amino alcohols

  摘要：

  The Mitsunobu reaction, utilizing several phenols, has been applied to a series of indan amino alcohols. An interesting example of configurational retention as a result of an aziridinium intermediate was discovered.

  DOI：

  10.1021/jo00002a033

文献信息

• Exploring Structural Diversity in Ligand Design: The Aminoindanol Case
  作者：Sergi Rodríguez-Escrich、Lluís Solà、Ciril Jimeno、Carles Rodríguez-Escrich、Miquel A. Pericàs

  DOI：10.1002/adsc.200800420

  日期：2008.10.6

  A series of enantiopure ligands based on the aminoindanol scaffold, but differing in regio- and stereochemistry has been synthesized. These ligands have been conveniently derivatized and their catalytic efficiency in different enantioselective reactions has been screened to determine privileged candidates with respect to regio- and stereochemistry for each considered process. The nature of the amino

  合成了一系列基于氨基茚满醇骨架的对映体纯配体，但在区域化学和立体化学上有所不同。这些配体已经被方便地衍生化，并且已经筛选了它们在不同对映选择性反应中的催化效率，从而为每个考虑的方法确定了关于区域化学和立体化学的优先候选者。氨基取代基的性质已针对特定应用进行了优化，这导致开发了一种通过还原胺化制备大体积双环胺的有效方法。
• Synthesis of 2-N,N-dialkylamino-1-aroyloxybenzocycloalkanes.
  作者：YASUFUMI HIRATA、ISAO YANAGISAWA、MASAAKI TAKEDA、HIROYOSHI INO、KOZO TAKAHASHI、MASUO MURAKAMI

  DOI：10.1248/cpb.25.1060

  日期：——

  Aroyl esters of 2-N, N-dialkylamino-1-benzocycloalkanols (6, 7), which may be considered to be semi-rigid cyclic analogs of procaine, were prepared to study the influence of the stereochemical relationship between the aroyloxy and the amino group on local anesthetic activity. The cis-compounds (6a-1, 6c-1) were more active than the corresponding trans-isomers (6b-1, 6d-1). Similarly, the optical isomers of cis-2-N, N-dimethylamino-1-benzoyloxy-1, 2, 3, 4-tetrahydronaphthalene (6c-1) differed in their activity with the l-isomer being more active. The reaction of 2-bromo-1-tetralol (9) with dimethylamine was also discussed.

  制备了 2-N，N-二烷基氨基-1-苯并环烷醇的丙酰基酯（6，7），以研究丙酰氧基和氨基之间的立体化学关系对局部麻醉活性的影响。顺式化合物（6a-1、6c-1）的活性高于相应的反式异构体（6b-1、6d-1）。同样，顺式-2-N，N-二甲基氨基-1-苯甲酰氧基-1，2，3，4-四氢萘的光学异构体（6c-1）的活性也不同，其中 l-异构体的活性更高。此外，还讨论了 2-溴-1-四氢萘酚（9）与二甲胺的反应。
• The Mitsunobu reaction of some indan amino alcohols
  作者：Jules Freedman、Mark J. Vaal、Edward W. Huber

  DOI：10.1021/jo00002a033

  日期：1991.1

  The Mitsunobu reaction, utilizing several phenols, has been applied to a series of indan amino alcohols. An interesting example of configurational retention as a result of an aziridinium intermediate was discovered.