1,4-Bis(bromomethyl)-2,3-(methylenedioxy)benzene | 162659-14-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1,4-Bis(bromomethyl)-2,3-(methylenedioxy)benzene
• 英文别名: 4,7-Bis(bromomethyl)-1,3-benzodioxole
• CAS: 162659-14-5
• 化学式: C₉H₈Br₂O₂
• 分子量: 307.969
• InChiKey: DKYRWEKHUZECTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-Bis(bromomethyl)-2,3-(methylenedioxy)benzene 在 盐酸 、 potassium tert-butylate 、 氨 、 叔丁胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.42h， 生成 6,7-(Methylenedioxy)-3,3,12,12-tetramethyl<4.4>paracyclophane-2,13-dione
  参考文献：
  名称：

  Synthesis and Conformational Analysis of 3,3,12,12-Tetramethyl[4.4]paracyclophane-2,13-dione

  摘要：

  Three [4.4]paracyclophanes (2-4) were synthesized by radical cyclization using the photoinduced S(RN)1 reaction. The structure of the most stable conformer of 4 was ascertained by means of X-ray crystallographic analysis, molecular mechanics calculations, and variable-temperature NMR spectra. The energy barriers to rotation of the two benzene rings in these compounds were obtained from an analysis of the temperature-dependent signals due to the 1,3-dioxolene and aromatic ring protons. Molecular mechanics calculations predicted three stable conformers for 4. Actually, three sets of signals were observed in its low-temperature H-1 NMR spectrum. An experimental technique was used in which crystals were dissolved in precooled solvent. In this manner, NMR signals were recorded due to the single conformer found in its crystalline state, which are identical to the major set of signals present in the original spectrum. The structures due to the other two sets of signals of 4 can;be successfully assigned by comparison of the low temperature H-1 NMR spectra of the two compounds (2 and 3). The interconversion pathways among these conformers were characterized.

  DOI：

  10.1021/jo00111a030
• 作为产物：
  描述：

  1,4-Bis(acetoxymethyl)-2,3-(methylenedioxy)benzene 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到1,4-Bis(bromomethyl)-2,3-(methylenedioxy)benzene
  参考文献：
  名称：

  Synthesis and Conformational Analysis of 3,3,12,12-Tetramethyl[4.4]paracyclophane-2,13-dione

  摘要：

  Three [4.4]paracyclophanes (2-4) were synthesized by radical cyclization using the photoinduced S(RN)1 reaction. The structure of the most stable conformer of 4 was ascertained by means of X-ray crystallographic analysis, molecular mechanics calculations, and variable-temperature NMR spectra. The energy barriers to rotation of the two benzene rings in these compounds were obtained from an analysis of the temperature-dependent signals due to the 1,3-dioxolene and aromatic ring protons. Molecular mechanics calculations predicted three stable conformers for 4. Actually, three sets of signals were observed in its low-temperature H-1 NMR spectrum. An experimental technique was used in which crystals were dissolved in precooled solvent. In this manner, NMR signals were recorded due to the single conformer found in its crystalline state, which are identical to the major set of signals present in the original spectrum. The structures due to the other two sets of signals of 4 can;be successfully assigned by comparison of the low temperature H-1 NMR spectra of the two compounds (2 and 3). The interconversion pathways among these conformers were characterized.

  DOI：

  10.1021/jo00111a030

文献信息

• METHODS OF DIAGNOSING, PREVENTING AND TREATING BONE MASS DISEASES
  申请人：Karsenty Gerard

  公开号：US20110152220A1

  公开（公告）日：2011-06-23

  The present invention provides methods and therapeutic agents for lowering or increasing serum serotonin levels in a patient in order to increase or decrease bone mass, respectively. In preferred embodiments, the patient is known to have, or to be at risk for, a low bone mass disease such as osteoporosis and the agents are TPH1 inhibitors or serotonin receptor antagonists.

  本发明提供了降低或增加患者血清5-羟色胺水平的方法和治疗剂，以分别增加或减少骨量。在优选实施方式中，患者已知患有或有患低骨量疾病（如骨质疏松症）的风险，药剂为TPH1抑制剂或5-羟色胺受体拮抗剂。
• METHODS OF DIAGNOSING, PREVENTING, AND TREATING BONE MASS DISEASES
  申请人：Karsenty Gerard

  公开号：US20150111908A1

  公开（公告）日：2015-04-23

  The present invention provides methods and therapeutic agents for lowering or increasing serum serotonin levels in a patient in order to increase or decrease bone mass, respectively. In preferred embodiments, the patient is known to have, or to be at risk for, a low bone mass disease such as osteoporosis and the agents are TPH1 inhibitors or serotonin receptor antagonists.

  本发明提供了降低或增加患者血清5-羟色胺水平以增加或减少骨量的方法和治疗剂。在优选实施例中，患者已知患有或有患低骨量疾病（如骨质疏松症）的风险，所使用的治疗剂为TPH1抑制剂或5-羟色胺受体拮抗剂。
• US8759364B2
  申请人：——

  公开号：US8759364B2

  公开（公告）日：2014-06-24
• Synthesis and Conformational Analysis of 3,3,12,12-Tetramethyl[4.4]paracyclophane-2,13-dione
  作者：Yoshimasa Fukazawa、Hiroaki Kitayama、Kazu Yasuhara、Kousaku Yoshimura、Shuji Usui

  DOI：10.1021/jo00111a030

  日期：1995.3

  Three [4.4]paracyclophanes (2-4) were synthesized by radical cyclization using the photoinduced S(RN)1 reaction. The structure of the most stable conformer of 4 was ascertained by means of X-ray crystallographic analysis, molecular mechanics calculations, and variable-temperature NMR spectra. The energy barriers to rotation of the two benzene rings in these compounds were obtained from an analysis of the temperature-dependent signals due to the 1,3-dioxolene and aromatic ring protons. Molecular mechanics calculations predicted three stable conformers for 4. Actually, three sets of signals were observed in its low-temperature H-1 NMR spectrum. An experimental technique was used in which crystals were dissolved in precooled solvent. In this manner, NMR signals were recorded due to the single conformer found in its crystalline state, which are identical to the major set of signals present in the original spectrum. The structures due to the other two sets of signals of 4 can;be successfully assigned by comparison of the low temperature H-1 NMR spectra of the two compounds (2 and 3). The interconversion pathways among these conformers were characterized.