5-溴-6-氯苯并[D][1,3]二氧杂环戊烯 | 233770-05-3

• 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
• 中文名称: 5-溴-6-氯苯并[D][1,3]二氧杂环戊烯
• 英文名称: 5-bromo-6-chloro-benzo[1,3]dioxole
• 英文别名: 5-Brom-6-chlor-benzo[1,3]dioxol；5-Bromo-6-chlorobenzo[d][1,3]dioxole；5-bromo-6-chloro-1,3-benzodioxole
• CAS: 233770-05-3
• 化学式: C₇H₄BrClO₂
• 分子量: 235.465
• InChiKey: VNFIRXCKAFPWRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  78 °C
• 沸点：
  281.8±40.0 °C(Predicted)
• 密度：
  1.828±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  5-溴-6-氯苯并[D][1,3]二氧杂环戊烯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium ethanolate 、 N,N-二异丙基乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 8-[(6-Chloro-1,3-benzodioxol-5-yl)sulfanyl]-9-(2-piperidin-4-ylethyl)purin-6-amine
  参考文献：
  名称：

  Discovery of (2S)-1-[4-(2-{6-Amino-8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9H-purin-9-yl}ethyl)piperidin-1-yl]-2-hydroxypropan-1-one (MPC-3100), a Purine-Based Hsp90 Inhibitor

  摘要：

  Modulation of Hsp90 (heat shock protein 90) function has been recognized as an attractive approach for cancer treatment, since many cancer cells depend on Hsp90 to maintain cellular homeostasis. This has spurred the search for small-molecule Hsp90 inhibitors. Here we describe our lead optimization studies centered on the purine-based Hsp90 inhibitor 28a containing a piperidine moiety at the purine N9 position. In this study, key SAR was established for the piperidine N-substituent and for the congeners of the 1,3-benzodioxole at C8. These efforts led to the identification of orally bioavailable 28g that exhibits good in vitro profiles and a characteristic molecular biomarker signature of Hsp90 inhibition both in vitro and in vivo. Favorable pharmacokinetic properties along with significant antitumor effects in multiple human cancer xenograft models led to the selection of 28g (MPC-3100) as a clinical candidate.

  DOI：

  10.1021/jm3004619
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 溴 、 sodium carbonate 作用下， 生成 5-溴-6-氯苯并[D][1,3]二氧杂环戊烯
  参考文献：
  名称：

  Orr; Robinson; Williams, Journal of the Chemical Society, 1917, vol. 111, p. 948

  摘要：

  DOI：

文献信息

• Bis(sym-collidine)bromine(I) hexafluorophosphate as oxidant
  作者：Gérard Rousseau、Sylvie Robin

  DOI：10.1016/s0040-4039(00)01598-7

  日期：2000.11

  Primary and secondary alcohols in solution in methylene chloride are oxidised with bis(sym-collidine)bromine(I) hexafluorophosphate in good yields to the carbonyl compounds. For secondary and tertiary alcohols in which one of the substituents is a 4-methoxyphenyl group the oxidation takes place by cleavage of the phenyl-sp3 carbon bond and formation of bromoanisole and carbonyl compounds.

  在二氯甲烷溶液中伯醇和仲醇被氧化与双（符号-collidine）溴（I）以良好的收率以羰基化合物六氟磷酸盐。对于其中一个取代基是4-甲氧基苯基的仲和叔醇，氧化是通过裂解苯基-sp 3碳键并形成溴茴香醚和羰基化合物来进行的。
• One-Pot Alkene Hydroboration/Palladium-Catalyzed Migratory Suzuki–Miyaura Cross-Coupling
  作者：Yann Baumgartner、Olivier Baudoin

  DOI：10.1021/acscatal.0c02755

  日期：2020.9.18

  powerful approach toward the functionalization of C–H bonds remote to a functional group. Whereas various Pd-catalyzed migratory cross-couplings have been developed in the past years, the design of an efficient migratory version of the popular Suzuki–Miyaura cross-coupling has remained elusive. The current article reports a one-pot procedure consisting of alkene hydroboration and migratory Suzuki–Miyaura

  链走是实现远离功能团的C–H键功能化的有效方法。尽管在过去的几年中开发了各种Pd催化的迁移交叉偶联剂，但仍然无法实现流行的Suzuki-Miyaura交叉偶联剂的高效迁移形式的设计。本文报道了一种一锅法，该方法包括烯烃硼氢化和所得烷基硼酸中间体的迁移Suzuki-Miyaura偶联。通过使用P（t -Bu）2获得了对初始烯烃的苄基位置的高区域选择性我作为配体和一个邻位取代的芳基亲电试剂。证明了从烯烃的位置和几何异构体的区域收敛性和远距离迁移。机理研究表明，迁移是通过部分可逆的非离解机制发生的。
• DIHYDROPYRAZOLE GPR40 MODULATORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP2925749A1

  公开（公告）日：2015-10-07
• US9604964B2
  申请人：——

  公开号：US9604964B2

  公开（公告）日：2017-03-28
• [EN] 8-AZABICYCLO(3.2.1)OCT-2-ENE DERIVATIVES AS PESTICIDES<br/>[FR] DERIVES DE 8-AZABICYCLO(3.2.1)OCT-2-ENE CONVENANT COMME PESTICIDES
  申请人：ZENECA LIMITED

  公开号：WO1999038865A1

  公开（公告）日：1999-08-05

  (EN) A compound of formula (I), wherein one of R1 and R2 is hydrogen and the other is a phenyl, pyridyl, pyrimidinyl, pyrazinyl, thienyl, thiazolyl, benzoxazol-2-one or benzimidazolin-2-one ring, said ring being optionally substituted with halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C2-6 alkenyl, C2-6 alkynyl, hydroxy, nitro, cyano or methylenedioxy; R is hydrogen, formyl, C1-6 alkyl (optionally substituted with cyano, CO2(C1-6 alkyl) or phenyl (itself optionally substituted with halogen, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl or C1-6 haloalkoxy)), CH2(C1-6 haloalkyl), CO2(C1-6 alkyl), CO2(C2-6 alkenyl), CH2(C2-6 alkenyl), CH2(C2-6 alkynyl), benzyl (wherein the phenyl ring is optionally substituted with halogen or C1-4 alkyl) or XR3; X is O or NR4; R3 and R4 are, independently, hydrogen, cyano, C1-6 alkyl (optionally substituted with halogen, cyano, CO2(C1-6 alkyl) or phenyl (itself optionally substituted with halogen, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl or C1-6 haloalkoxy)), phenyl (itself optionally substituted with halogen, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl or C1-6 haloalkoxy), C2-6 alkenyl or C2-6 alkynyl; or an acid addition salt or N-oxide thereof, processes for preparing these compounds, compositions comprising them and methods of using them to combat or control insects, acarines, nematodes or molluscs.(FR) La présente invention concerne un composé représenté par la formule générale (I) l'un de ses sels d'addition acides ou l'un de ses N-oxides. Dans cette formule, R1 et R2 sont l'un hydrogène et l'autre un cycle phényle, pyridyle, pyrimidinyle, pyrazinyle, thiényle, thiazolyle, benzoxazol-2-one ou benzimidazolin-2-one. Ce cycle est fonctionnellement substitué par un halogène, C1-6 alkyle, C1-6 haloalkyle, C1-6 alcoxy, C1-6 haloalcoxy, C2-6 alcényle, C2-6 alkynyle, hydroxy, nitro, cyano ou méhylènedioxy. R est hydrogène, formyle, C1-6 alkyle (éventuellement substitué par un cyano, CO2(C1-6 alkyle) ou phényle (lui-même éventuellement substitué par un halogène, C1-6 alkyle, C1-6 alcoxy, C1-6 haloalkyle ou C1-6 haloalcoxy)), CH2(C1-6 haloalkyle), CO2(C1-6 alkyle), CO2(C2-6 alcényle), CH2(C2-6 alcényle), CH2(C2-6 alkynyle), benzyle (où le cycle phényle est éventuellement substitué par un halogène ou C1-4 alkyle) ou XR3. X est O ou NR4. R3 et R4 sont, indépendamment, hydrogène, cyano, C1-6 alkyle (éventuellement substitué par un halogène, cyano, CO2(C1-6 alkyle) ou phényle (lui-même éventuellement substitué par un halogène, C1-6 alkyle, C1-6 alcoxy, C1-6 haloalkyle ou C1-6 haloalcoxy)), phényle (lui-même éventuellement substitué par un halogène, C1-6 alkyle, C1-6 alcoxy, C1-6 haloalkyle ou C1-6 haloalcoxy), C2-6 alcényle ou C2-6 alkynyle. L'invention concerne également des procédés d'élaboration de ces composés, des compositions intégrant ces composés et des procédés permettant d'utiliser ces dérivés pour lutter contre des insectes, des acariens, des nématodes ou des mollusques.