5-bromodibenzosuberane | 259546-08-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 5-bromodibenzosuberane
• 英文别名: suberanyl bromide；2-Bromotricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaene
• CAS: 259546-08-2
• 化学式: C₁₅H₁₃Br
• 分子量: 273.172
• InChiKey: DZRGXMASVMFDSG-UHFFFAOYSA-N

物化性质

• 沸点：
  328.1±31.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5-bromodibenzosuberane 生成 (10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-phosphonic acid
  参考文献：
  名称：

  Benzylphosphonic acid inhibitors of human prostatic acid phosphatase

  摘要：

  A series of alpha-substituted benzylphosphonic acids is described as inhibitors of human prostatic acid phosphatase, an enzyme which has been used as a model to study aryl phosphatases. The most potent inhibitors in this series are 2-trifluoromethylbenzhydrylphosphonic acid (9 mu M), and alpha-(2-phenylethyl)benzylphosphonic acid (14 mu M) The structure-activity studies suggest that bulk tolerance beyond the phosphate binding area limits the steric or hydrophobic contribution to inhibitor potency achieved through alpha-carbon substitution.

  DOI：

  10.1016/0960-894x(96)00018-2
• 作为产物：
  描述：

  二苯并噻唑 在 乙酰溴 作用下， 反应 0.33h， 以79%的产率得到5-bromodibenzosuberane
  参考文献：
  名称：

  REACTIVITY OF METHYLENETRIPHENYLPHOSPHORANES HAVING TWO PHENYL GROUPS CONSTRAINED WITH ETHANO OR ETHENO BRIDGE

  摘要：

  Methylenetriphenylphosphoranes having two phenyl groups tied together with ethano or etheno bridge were prepared by conventional ways in order to suppress delocalization of an ylide-carbanion by deforming geometrical arrangement of phenyl groups from that of the diarylmethylene derivative and hence to elevate reactivities of diarylmethylenephosphoranes. These P-ylides were, however, still unreactive with usual aldehydes and ketones. The reasons, are deliberated by molecular orbital calculations and the P-31-NMR data. The HOMO orbitals of ethano-bridged and etheno-bridged diarylmethylenephosphoranes are located on a monoarylcarbanion and a carbanion, respectively. Although these tendencies are auspicious to enhance the Wittig reactivity of them, the electron densities of the ylidic carbons are still insufficient. P-31-NMR chemical shifts of the ylides revealed that the objective P-ylides do not have a large extent of the ylide-contribution in the ylide-yllene resonance. Meanwhile, they reacted readily with tetrahalo o-quinones to give 1,3-dioxoles in good yields. Thermochromic behavior of one of the precursors, dibenzosuberenylphosphonium salt, was observed at 80 degreesC in acetonitrile in the presence of trace perchloric acid. The colored species is elucidated as dibenzo[a,e]tropylium cation.

  DOI：

  10.1080/10426509808036985

文献信息

• Process for the preparation of substituted pyrrolidine neuraminidase inhibitors
  申请人：——

  公开号：US20030055297A1

  公开（公告）日：2003-03-20

  A process for the preparation of neuraminidase inhibitors having structural formula (28) 1 or therapeutically acceptable salts thereof, in which R 1 is alkyl, cycloalkyl, cycloalkylalkyl, or arylalkyl; R 2 is alkyl, cycloalkyl, cycloalkylalkyl, or arylalkyl; R 4 is alkyl, cycloalkyalkyl, or aryl-(C 2 -C 4 -alkyl); R 10 is methyl, ethyl, iso-propyl, or vinyl; and R 12 is hydrogen or alkyl and intermediates useful for the process are disclosed.

  一种用于制备具有结构式（28）1或其治疗上可接受的盐的神经氨酸酶抑制剂的方法，其中R1是烷基，环烷基，环烷基烷基或芳基烷基；R2是烷基，环烷基，环烷基烷基或芳基烷基；R4是烷基，环烷烷基或芳基（C2-C4-烷基）；R10是甲基，乙基，异丙基或乙烯基；和R12是氢或烷基，公开了用于该方法的中间体。
• Novel Heterocyclic Analogs of Trityl Radicals: Synthesis and Dimerization of Diarylmethyl-1H-1,2,4-triazoles and Diarylmethyl-2H-phenanthro[9,10-d]-1,2,3-triazoles
  作者：Alan R. Katritzky、Baozhen Yang、David P. M. Pleynet、Jin Wang

  DOI：10.3987/com-99-s9

  日期：——
• [EN] PROCESS FOR THE PREPARATION OF SUBSTITUTED PYRROLIDINE NEURAMINIDASE INHIBITORS<br/>[FR] PROCEDE DE PREPARATION D'INHIBITEURS DE PYRROLIDINE NEURAMINIDASE SUBSTITUE
  申请人：ABBOTT LAB

  公开号：WO2002081441A1

  公开（公告）日：2002-10-17

  A process for the preparation of neuraminidase inhibitors having structural formula (28) or therapeutically acceptable salts thereof, in which R1 is alkyl, cycloalkyl, cycloalkylalkyl, or arylalkyl; R2 is alkyl, cycloalkyl, cycloalkylalkyl, or arylalkyl; R4 is alkyl, cycloalkyalkyl, or aryl-(C2-C4-alkyl); R10 is methyl, ethyl, iso-propyl, or vinyl; and R12 is hydrogen or alkyl and intermediates useful for the process are disclosed.
• Benzylphosphonic acid inhibitors of human prostatic acid phosphatase
  作者：Charles F. Schwender、Scott A. Beers、Elizabeth A. Malloy、Jacqueline J. Cinicola、David J. Wustrow、Keith D. Demarest、Jerold Jordan

  DOI：10.1016/0960-894x(96)00018-2

  日期：1996.2

  A series of alpha-substituted benzylphosphonic acids is described as inhibitors of human prostatic acid phosphatase, an enzyme which has been used as a model to study aryl phosphatases. The most potent inhibitors in this series are 2-trifluoromethylbenzhydrylphosphonic acid (9 mu M), and alpha-(2-phenylethyl)benzylphosphonic acid (14 mu M) The structure-activity studies suggest that bulk tolerance beyond the phosphate binding area limits the steric or hydrophobic contribution to inhibitor potency achieved through alpha-carbon substitution.
• REACTIVITY OF METHYLENETRIPHENYLPHOSPHORANES HAVING TWO PHENYL GROUPS CONSTRAINED WITH ETHANO OR ETHENO BRIDGE
  作者：Yasuhiko Kawamura、Yasunori Iwano、Noboru Watanabe、Tokunaru Horie、Masao Tsukayama

  DOI：10.1080/10426509808036985

  日期：1998.1.1

  Methylenetriphenylphosphoranes having two phenyl groups tied together with ethano or etheno bridge were prepared by conventional ways in order to suppress delocalization of an ylide-carbanion by deforming geometrical arrangement of phenyl groups from that of the diarylmethylene derivative and hence to elevate reactivities of diarylmethylenephosphoranes. These P-ylides were, however, still unreactive with usual aldehydes and ketones. The reasons, are deliberated by molecular orbital calculations and the P-31-NMR data. The HOMO orbitals of ethano-bridged and etheno-bridged diarylmethylenephosphoranes are located on a monoarylcarbanion and a carbanion, respectively. Although these tendencies are auspicious to enhance the Wittig reactivity of them, the electron densities of the ylidic carbons are still insufficient. P-31-NMR chemical shifts of the ylides revealed that the objective P-ylides do not have a large extent of the ylide-contribution in the ylide-yllene resonance. Meanwhile, they reacted readily with tetrahalo o-quinones to give 1,3-dioxoles in good yields. Thermochromic behavior of one of the precursors, dibenzosuberenylphosphonium salt, was observed at 80 degreesC in acetonitrile in the presence of trace perchloric acid. The colored species is elucidated as dibenzo[a,e]tropylium cation.