6-溴-2,2-二甲基-2H-苯并吡喃 | 82305-04-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 6-溴-2,2-二甲基-2H-苯并吡喃
• 中文别名: 6-溴-2,2-二甲基-2H-色烯
• 英文名称: 6-bromo-2,2-dimethyl-2H-chromene
• 英文别名: 6-bromo-2,2-dimethylchromene；6-bromo-2,2-dimethyl-2H-benzo[b]pyran
• CAS: 82305-04-2
• 化学式: C₁₁H₁₁BrO
• mdl: MFCD11847611
• 分子量: 239.112
• InChiKey: FHBXFINOQUIMDK-UHFFFAOYSA-N

物化性质

• 熔点：
  143-146℃ (19 TORR)
• 沸点：
  286℃
• 密度：
  1.364
• 闪点：
  113℃

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2903399090

反应信息

• 作为反应物：
  描述：

  6-溴-2,2-二甲基-2H-苯并吡喃 在 正丁基锂 、 水 作用下， 生成 2,2,-二甲基-2H-苯并吡喃
  参考文献：
  名称：

  Alberola, Angel; Calvo, Blanca; Gonzalez-Ortega, Alfonso, Heterocycles, 1994, vol. 38, # 4, p. 819 - 832

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2-二甲基-4-氧代色满-7-甲腈 在 钾硼氢 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 5.5h， 生成 6-溴-2,2-二甲基-2H-苯并吡喃
  参考文献：
  名称：

  Relaxant activity of 4-amido-3,4-dihydro-2H-1-benzopyran-3-ols and 4-amido-2H-1-benzopyrans on guinea pig isolated trachealis

  摘要：

  A series of 4-amido-3,4-dihydro-2H-1-benzopyran-3-ols and 4-amido-2H-1-benzopyrans related to the potassium channel activator cromakalim have been prepared and evaluated for their relaxant activity in guinea pig isolated tracheal spirals. Several analogues show enhanced relaxant activity relative to cromakalim in this preparation and the rank order of potency for those substituents investigated at C-6 was CF3 greater than CN greater than C2H5 greater than aza greater than or equal to CH3. One compound, trans-3,4-dihydro-2,2-dimethyl-4-(2-oxopiperidin-1-yl)-7-(trifluor omethyl)-2H- 1-benzopyran-3-ol (24), was resolved into its two enantiomers and the activity was shown to reside essentially in the (+)-isomer, adding further support to the suggestion that the smooth muscle receptor for these potassium channel activators is stereoselective.

  DOI：

  10.1021/jm00173a019

文献信息

• Thieme Chemistry Journal Awardees - Where Are They Now? Microwave-Assisted Rhodium-Catalyzed Decarbonylation of Functionalized 3-Formyl-2<i>H</i>-chromenes: A Sequence for Functionalized Chromenes like Deoxycordiachromene
  作者：Stefan Bräse、Manuel Bröhmer、Nicole Volz

  DOI：10.1055/s-0029-1217179

  日期：——

  3-Formyl-2H-chromenes which are readily accessible through an oxa-Michael reaction of salicylaldehydes and α,β-unsaturated aldehydes undergo a smooth decarbonylation reaction upon treatment with rhodium catalysts. With our method, a great variety of functionalized chromenes is accessible in a two-step sequence from salicylaldehydes.

  3-甲酰基-2H-色烯可通过水合物迈克尔反应，由水杨醛和α，β-不饱和醛轻易制得。这些化合物在铑催化剂作用下会顺利进行脱羰反应。运用我们的方法，可通过水杨醛的两步反应，大量制备功能化色烯。
• Synthesis of Metal–(Pentadentate-Salen) Complexes: Asymmetric Epoxidation with Aqueous Hydrogen Peroxide and Asymmetric Cyclopropanation (salenH2:N,N′-bis(salicylidene)ethylene-1,2-diamine)
  作者：Hiroaki Shitama、Tsutomu Katsuki

  DOI：10.1002/chem.200601420

  日期：2007.6.4

  manganese(III) and cobalt(II) complexes, in which the fifth ligand is expected to intramolecularly coordinate to the metal center and exert a trans effect. Indeed, high enantioselectivity has been achieved in epoxidations using aqueous hydrogen peroxide as the terminal oxidant and in cyclopropanations with these complexes as catalysts. In general, metallosalen-catalyzed reactions have been carried out

  众所周知，使用金属氯辛烯（salenH（2）：N，N'-双（水杨基）乙烯-1,2-二胺）配合物作为催化剂的环氧化和环丙烷化的速率和立体化学结果会受到反式作用的影响。复杂的顶端配体。考虑到这种反式效应，我们合成了带有咪唑或吡啶衍生物作为第五配位基团的旋光五齿萨伦配体，并制备了相应的锰（III）和钴（II）配合物，其中第五配体为预期在分子内与金属中心配位并产生反式效应。实际上，在使用过氧化氢水溶液作为末端氧化剂的环氧化反应中以及在使用这些配合物作为催化剂的环丙烷化反应中，已经实现了高对映选择性。一般来说，在过量供体配体的存在下进行了金属氯烯催化的反应。然而，本反应不需要添加任何额外的供体配体。
• Benzopyranes as potassium channel openers
  申请人：Pfizer Inc.

  公开号：US05677324A1

  公开（公告）日：1997-10-14

  The present invention relates to compounds of formula (I) and the pharmaceutically acceptable salts thereof, wherein the dashed line represents an optional covalent bond; X is O, NH, S or a direct link; R.sup.3 is hydroxy when the dashed line does not represent a covalent bond and R.sup.3 is absent when the dashed line represents a covalent bond; R.sup.4 is (a), when X is O, a group of formula (i), (b), when X is O, NH or S, optionally substituted hydroxyphenyl, (c) an optionally substituted 4- to 7-membered heterocyclic ring, or (d), when X is NH, a group of formula (ii). The compounds are useful for the treatment of disease associated with the altered tone or motility of smooth muscle. ##STR1##

  本发明涉及式(I)的化合物及其药学上可接受的盐，其中虚线代表可选的共价键；X为O、NH、S或直接连接；当虚线不代表共价键时，R.sup.3为羟基，当虚线代表共价键时，R.sup.3不存在；当X为O时，R.sup.4为(a)，为式(i)的基团，当X为O、NH或S时，为可选取代的羟基苯基(b)，为可选取代的4-至7-成员杂环环(c)，或当X为NH时，为式(ii)的基团(d)。这些化合物对于治疗与平滑肌张力或运动异常相关的疾病是有用的。
• Asymmetric Counteranion-Directed Transition-Metal Catalysis: Enantioselective Epoxidation of Alkenes with Manganese(III) Salen Phosphate Complexes
  作者：Saihu Liao、Benjamin List

  DOI：10.1002/anie.200905332

  日期：2010.1.12

  Paired up: A highly active and enantioselective ion‐pair epoxidation catalyst, consisting of an achiral MnIII–salen complex and a chiral phosphate counteranion, mediates the epoxidization of a wide range of alkenes with high yields and enantioselectivities (see scheme). The unique role of the counteranion is to stabilize an enantiomorphic conformation of the cationic Mn catalyst.

  配对：高活性和对映选择性离子对环氧化催化剂，由非手性Mn III -salen配合物和手性磷酸抗衡阴离子组成，可介导高产率和对映选择性的多种烯烃的环氧化。抗衡阴离子的独特作用是稳定阳离子Mn催化剂的对映体构象。
• Natural Product-like Combinatorial Libraries Based on Privileged Structures. 1. General Principles and Solid-Phase Synthesis of Benzopyrans
  作者：K. C. Nicolaou、J. A. Pfefferkorn、A. J. Roecker、G.-Q. Cao、S. Barluenga、H. J. Mitchell

  DOI：10.1021/ja002033k

  日期：2000.10.1

  report a novel strategy for the design and construction of natural and natural product-like libraries based on the principle of privileged structures, a term originally introduced to describe structural motifs capable of interacting with a variety of unrelated molecular targets. The identification of such privileged structures in natural products is discussed, and subsequently the 2,2-dimethylbenzopyran

  在此，我们报告了一种基于特权结构原理设计和构建天然和天然产物类库的新策略，该术语最初用于描述能够与各种不相关的分子靶标相互作用的结构基序。讨论了天然产物中此类特权结构的鉴定，随后选择 2,2-二甲基苯并吡喃部分作为通过该策略构建类天然产物库的初始模板。最初，采用独特的环加载策略开发了苯并吡喃基序的新型固相合成，该策略依赖于使用新的聚苯乙烯基溴化硒树脂。一旦确定了这些苯并吡喃的加载、加工和裂解，