9-chloroisocolchicide | 20564-86-7

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 9-chloroisocolchicide
• 英文别名: N-[(7S)-9-chloro-1,2,3-trimethoxy-10-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• CAS: 20564-86-7
• 化学式: C₂₁H₂₂ClNO₅
• 分子量: 403.862
• InChiKey: VPKXSFUJBXNQRE-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  哌啶 、 9-chloroisocolchicide 以 二甲基亚砜 为溶剂， 以10%的产率得到11-piperidinoisocolchicide
  参考文献：
  名称：

  ipso-vs. tele-Nucleophilic substitution by piperidine on isocolchicides and colchicides bearing an α-leaving group

  摘要：

  Product studies of the reactions of piperidine with colchicides carrying a C-10 nucleofugic group show that only ipso substitution occurs. For isocolchicides carrying an X nucleofugic group at C-9, similar behaviour was observed for X = F, OTs or OMe, while for X = SMe, SOMe or Cl tele substitution (at C-ll) competes with ipso substitution. These results together with the observation that the reaction rates for the two series are similar, may be useful in guiding the refunctionalization of similar compounds.

  DOI：

  10.1039/p19950002657
• 作为产物：
  描述：

  Benzenesulfonic acid (S)-7-acetylamino-1,2,3-trimethoxy-10-oxo-5,6,7,10-tetrahydro-benzo[a]heptalen-9-yl ester 在 三氟化硼乙醚 、 lithium chloride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以66%的产率得到9-chloroisocolchicide
  参考文献：
  名称：

  A General Entry to 10-Halocolchicides and 9-Haloisocolchicides

  摘要：

  Readily accessible 10-tosyloxycolchicide (1) and LiX (X=Cl or Br or I) in MeOH/BF3.Et2O at reflux give 10-chloro- (2), 10-bromo- (4), or 10-iodocolchicide (5), in good yields. 9-Chloro- (7) and 9-bromoisocolchidide (8) can be similarly obtained front 9-tosyloxyisocolchidide (6) and the method applies also to troponoids.

  DOI：

  10.1080/00397919708005641

文献信息

• Synthesis of 1,3-diazaazulene derivatives of colchicinoids and isocolchicinoids via ipso- or tele-substitution-condensation with amidines
  作者：Marino Cavazza、Francesco Pietra

  DOI：10.1016/s0040-4020(98)00856-4

  日期：1998.11

  nsation products (e.g. 7) are best obtained from cycloheptatrienone-ring deactivated substrates (e.g. 4), whereas isomeric tele-substitution-condensation products (e.g. 13), are best accessible from cycloheptatrienone-ring activated substrates (e.g. 10). Hydroxylic solvents inhibit tele-substitution-condensation, arguably by undergoing protonation in preference of the intermediate σ adduct.

  秋水仙碱和isocolchicinoids与无水苯，得到区域选择性1,3-二氮杂薁类衍生物脒缩合：本位3'-取代缩合产物（例如7），最好从cycloheptatrienone环得到的失活底物（例如4），而异构体远程3'-取代缩合产品（例如13）最好从环庚三烯酮环活化的底物（例如10）获得。羟基溶剂可以抑制远程取代缩合，这可以通过优先于中间σ加合物进行质子化来解决。
• ipso-vs. tele-Nucleophilic substitution by piperidine on isocolchicides and colchicides bearing an α-leaving group
  作者：Marino Cavazza、Francesco Pietra

  DOI：10.1039/p19950002657

  日期：——

  Product studies of the reactions of piperidine with colchicides carrying a C-10 nucleofugic group show that only ipso substitution occurs. For isocolchicides carrying an X nucleofugic group at C-9, similar behaviour was observed for X = F, OTs or OMe, while for X = SMe, SOMe or Cl tele substitution (at C-ll) competes with ipso substitution. These results together with the observation that the reaction rates for the two series are similar, may be useful in guiding the refunctionalization of similar compounds.
• A General Entry to 10-Halocolchicides and 9-Haloisocolchicides
  作者：Marino Cavazza、Francesco Pietra

  DOI：10.1080/00397919708005641

  日期：1997.10

  Readily accessible 10-tosyloxycolchicide (1) and LiX (X=Cl or Br or I) in MeOH/BF3.Et2O at reflux give 10-chloro- (2), 10-bromo- (4), or 10-iodocolchicide (5), in good yields. 9-Chloro- (7) and 9-bromoisocolchidide (8) can be similarly obtained front 9-tosyloxyisocolchidide (6) and the method applies also to troponoids.