3-hydroxy-3-phenyl-2-propyl-2,3-dihydroisoindol-1-one | 27687-35-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-hydroxy-3-phenyl-2-propyl-2,3-dihydroisoindol-1-one
• 英文别名: 3-Hydroxy-3-phenyl-2-propyl-1-isoindolinone；3-hydroxy-3-phenyl-2-propylisoindol-1-one
• CAS: 27687-35-0
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: LWFZCJMPZMPKNL-UHFFFAOYSA-N

物化性质

• 熔点：
  231-232 °C
• 沸点：
  461.6±45.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-phenyl-2-propyl-2,3-dihydroisoindol-1-one 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以100%的产率得到2-n-Propyl-3-chlor-3-phenylisoindolinon
  参考文献：
  名称：

  Synthesis of 3-Alkoxy- and 3-Alkylamino-2-alkyl-3-arylisoindolinones

  摘要：

  溶剂控制的区域选择性使得3-氯异吲哚啉酮与初级胺的反应能够合理合成异吲哚啉酮，路线适合于平行组合化学。

  DOI：

  10.1055/s-1999-3116
• 作为产物：
  描述：

  邻苯甲酰苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 3-hydroxy-3-phenyl-2-propyl-2,3-dihydroisoindol-1-one
  参考文献：
  名称：

  异吲哚啉酮脱硫的总自发分解

  摘要：

  分离的：3-羟基-3-苯基异吲哚啉-1-酮已通过动态优先结晶分离。在碱性条件下，这些化合物通过非手性中间体通过开环和闭环反应有效地消旋。在搅拌下从含有1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）的甲苯溶液中结晶并蒸发溶剂，可定量得到具有高ee值的光学活性晶体。

  DOI：

  10.1002/anie.201205097

文献信息

• [EN] ISOINDOLIN-1-ONE DERIVATIVES<br/>[FR] DÉRIVÉS D'ISOINDOLIN-1-ONE
  申请人：CANCER REC TECH LTD

  公开号：WO2006024837A1

  公开（公告）日：2006-03-09

  A compound of formula (1) or a prodrug and/or pharmaceutically acceptable salt thereof, wherein X is selected from O, N or S; R1 is selected from hydrogen, halo, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted hydroxyalkyl, substituted or unsubstituted alkylamine, alkoxy, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroaralkyl; R2 is selected from hydrogen, halo, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted hydroxyalkyl substituted or unsubstituted alkylamine, alkoxy, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroalkyl; R3 is selected from hydrogen, halo, hydroxy, substituted or unsubstituted alloy substituted or unsubstituted hydroxyalkyl, substituted or unsubstituted alkylamine alkoxy, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroalkyl; and R4-R7, is used to represent groups R4, R5, R6 and R7 which are independently selected from H, OH, alkyl, alkoxy, alkylamine, hydroxyalkyl, halo, CF3, NH2, NO2, COOH, C=0.

  式（1）的化合物或其前药和/或药用可接受的盐，其中X选择自O、N或S；R1选择自氢、卤素、羟基、取代或未取代的烷基、取代或未取代的羟基烷基、取代或未取代的烷基胺、烷氧基、取代或未取代的芳基或杂环芳基、取代或未取代的芳基或杂环芳基；R2选择自氢、卤素、羟基、取代或未取代的烷基、取代或未取代的羟基烷基、取代或未取代的烷基胺、烷氧基、取代或未取代的芳基或杂环芳基、取代或未取代的芳基或杂环芳基；R3选择自氢、卤素、羟基、取代或未取代的合金取代或未取代的羟基烷基、取代或未取代的烷基胺烷氧基、取代或未取代的芳基或杂环芳基、取代或未取代的芳基或杂环芳基；R4-R7，用于表示独立选择自H、OH、烷基、烷氧基、烷基胺、羟基烷基、卤素、CF3、NH2、NO2、COOH、C=0的基团R4、R5、R6和R7。
• Pseudoacids. II. 2-Acylbenzoic Acid Derivatives
  作者：E. J. Valente、S. B. Martin、L. D. Sullivan

  DOI：10.1107/s0108768197012020

  日期：1998.6.1

  Structures of derivatives of cyclic o-acylbenzoic acids, including the chloride, endo- and exocyclic amides, esters and anhydrides, are examined. 3-Chloro-1(3H)-isobenzofuranone (1), orthorhombic, Pbca, a = 11.616 (5), b = 8.120 (3), c = 15.640 (9) Å; 3-methoxy-3-phenyl-1(3H)-isobenzofuranone (3), orthorhombic, P2₁2₁2₁, a = 6.923 (2), b = 8.291 (4), c = 21.551 (8) Å; 3-hydroxy-3-phenyl-N-propyl-1(3H)-isoindolone (4), orthorhombic, P2₁2₁2₁, a = 8.662 (4), b = 9.551 (7), c = 17.649 (14) Å; 3-(N-morpholino)-1(3H)-isobenzofuranone (5), triclinic, P1¯, a = 6.172 (4), b = 11.163 (7), c = 17.33 (2) Å, α = 105.91 (6), β = 99.85 (6), γ = 97.57 (5)°; 3-(2′-benzoylbenzoyloxy)-3-phenyl-1(3H)-isobenzofuranone (7), triclinic, P1¯, a = 9.694 (3), b = 10.505 (4), c = 11.163 (4) Å, α = 80.58 (3), β = 80.41 (3), γ = 76.49 (3)°; bis[1(3H)-isobenzofuranone-3-yl]ether (8), monoclinic, I2/a, a = 15.31 (2), b = 6.111 (12), c = 28.30 (5) Å, β = 101.61 (12)°. An open oxoacid tertiary amide is also described: N-morpholino 2′-benzoylbenzamide (6): monoclinic, P2₁/c, a = 6.844 (4), b = 15.696 (8), c = 14.154 (7) Å, β = 99.43 (4)°. Pseudoacid derivatives form planar isobenzofuran and isoindole rings, and the former aldehyde/ketone carbon–heteroatom endocyclic and exocyclic bond distances show bond length variations which correlate with the relative basicities of the attached groups. Structures of both endocyclic and exocyclic nitrogen pseudoamides are reported as well as examples of the normal–pseudoanhydride and the dipseudoanhydride.

  研究了环状邻酰基苯甲酸衍生物的结构，包括氯化物、内环和外环酰胺、酯和酸酐。3-氯-1(3H)-异苯并呋喃酮 (1)，正方体，Pbca，a = 11.616 (5)，b = 8.120 (3)，c = 15.640 (9) Å；3-甲氧基-3-苯基-1(3H)-异苯并呋喃酮 (3)，正方体，P212121，a = 6.923 (2)，b = 8.291 (4)，c = 21.551 (8) Å；3-羟基-3-苯基-N-丙基-1(3H)-异吲哚酮 (4)，正方晶，P212121，a = 8.662 (4)，b = 9.551 (7)，c = 17.649 (14) Å；3-(N-吗啉基)-1(3H)-异苯并呋喃酮 (5)，三棱晶，P1¯，a = 6.172 (4)，b = 11.163 (7)，c = 17.33 (2) Å，α = 105.91 (6)，β = 99.85 (6)，γ = 97.57 (5)°；3-(2′-苯甲酰苯甲酰氧基)-3-苯基-1(3H)-异苯并呋喃酮(7)，三棱，P1¯，a = 9.694 (3)，b = 10.505 (4)，c = 11.163 (4) Å，α = 80.58 (3)，β = 80.41 (3)，γ = 76.49 (3)°；双[1(3H)-异苯并呋喃酮-3-基]醚 (8)，单斜，I2/a，a = 15.31 (2)，b = 6.111 (12)，c = 28.30 (5) Å，β = 101.61 (12)°。此外，还描述了一种开放的草酸叔酰胺：N-吗啉基 2′-苯甲酰苯甲酰胺 (6)：单斜，P21/c，a = 6.844 (4)，b = 15.696 (8)，c = 14.154 (7) Å，β = 99.43 (4)°。伪酸衍生物形成平面异苯并呋喃环和异吲哚环，前醛/酮碳-杂原子内环和外环键距显示出键长变化，这与所附基团的相对碱性有关。报告了内环和外环氮假酰胺的结构，以及正常假酸酐和二假酸酐的实例。
• Reaction of 3-Hydroxyisoindolin-1-ones with Lawesson Reagent. Synthesis of Isoindoline-1-thiones
  作者：Takehiko Nishio、Norikazu Okuda、Yo-ichi Mori、Choji Kashima

  DOI：10.1055/s-1989-27264

  日期：——

  Treatment of 3-hydroxyisoindolin-1-ones 1 with Lawesson reagent gave isoindoline-1-thiones 2, by direct thionation and reductive elimination of hydroxy group, in good yields.

  用 Lawesson 试剂处理 3-羟基异吲哚啉-1-酮 1，通过直接硫化和还原消除羟基，得到异吲哚啉-1-硫酮 2，收率良好。
• Isoindolin-1-One Derivatives
  申请人：Willems Hendrika Maria Gerarda

  公开号：US20080261917A1

  公开（公告）日：2008-10-23

  A compound of formula or a prodrug and/or a pharmaceutically acceptable salt thereof, wherein X is O, N or S; R 1 is hydrogen, halo, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted hydroxyalkyl, substituted or unsubstituted alkylamine, alkoxy, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroaralkyl; R 2 is hydrogen, halo, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted hydroxyalkyl substituted or unsubstituted alkylamine, alkoxy, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroalkyl; R 3 is hydrogen, halo, hydroxy, substituted or unsubstituted alloy substituted or unsubstituted hydroxyalkyl, substituted or unsubstituted alkylamine alkoxy, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroalkyl; and R 4 -R 7 , is used to represent groups R 4 , R 5 , R 6 and R 7 which are H, OH, alkyl, alkoxy, alkylamine, hydroxyalkyl, halo, CF 3 , NH 2 , NO 2 , COOH, C=0.

  该化合物的化学式为，或其前体药物和/或其药学上可接受的盐，其中X为O、N或S；R1为氢、卤、羟基、取代或未取代的烷基、取代或未取代的羟基烷基、取代或未取代的烷基胺、烷氧基、取代或未取代的芳基或杂环芳基、取代或未取代的芳基烷基或杂环芳基烷基；R2为氢、卤、羟基、取代或未取代的烷基、取代或未取代的羟基烷基、取代或未取代的烷基胺、烷氧基、取代或未取代的芳基或杂环芳基、取代或未取代的芳基烷基或杂环芳基烷基；R3为氢、卤、羟基、取代或未取代的烷基、取代或未取代的羟基烷基、取代或未取代的烷基胺、烷氧基、取代或未取代的芳基或杂环芳基、取代或未取代的芳基烷基或杂环芳基烷基；R4-R7用于代表R4、R5、R6和R7的基团，其为H、OH、烷基、烷氧基、烷基胺、羟基烷基、卤、CF3、NH2、NO2、COOH、C=0。
• Nishio, Takehiko; Yamamoto, Hiroshi, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 883 - 892
  作者：Nishio, Takehiko、Yamamoto, Hiroshi

  DOI：——

  日期：——