1-(2-bromoethyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane | 135956-78-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-bromoethyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane
• CAS: 135956-78-4
• 化学式: C₈H₁₃BrO₃
• 分子量: 237.093
• InChiKey: KGQIKJXPSPZGBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-bromoethyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane 在 碳酸氢钠 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 22.0h， 生成 1-(2-triphenylphosphoniumethyl)-4-methyl-2,6,7-trioxabicyclo<2.2.2>octane iodide
  参考文献：
  名称：

  有机合成中的热稳定酶。5.使用tbadh生成的双官能丁烯完全合成S-（+）-Z-dodec-3-en-11-olide（ferrulactone II）。

  摘要：

  （S）-（+）-ferrulactone（2）的全合成是雄性扁平甲虫Cryptolestes ferrugineus（Stephens）产生的几种协同聚集信息素之一，是通过五步合成以极高的光学纯度实现的（>从（S）-（+）-甲基-8-羟基壬酸酯（5）和三碳Wittig试剂11开始，获得99％ee）和17.5％的化学收率。通过用布氏嗜热厌氧菌醇脱氢酶（TBADH）对映选择性还原，由8-氧代壬酸甲酯获得九碳双功能Chiron 5。

  DOI：

  10.1016/s0040-4020(01)86469-3
• 作为产物：
  描述：

  1,1,1-三(羟甲基)乙烷 在 吡啶 、 三氟化硼乙醚 、 三乙胺 、 碳酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-(2-bromoethyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane
  参考文献：
  名称：

  Synthese von ?-Acetyl-?-methylenpolyencarbons�ureestern

  摘要：

  The alpha-methylenpolyene carboxylic acids 1 and 2 are highly active against Gram-positive bacteria. If this activity arises from an interference with the cell membranes, then an abrupt change in biological properties is to be expected with growing chain length of simple model compounds. To make these tests possible, we describe here the synthesis of a series of homologue esters of type 40. Their synthesis was achieved by Wittig reactions of polyene alpha,omega-dialdehydes 6 with acetyl-methylentriphenylphosphoran 5a and the protected carboxymethylmethylen triphenylphosphonium salt 8.

  DOI：

  10.1002/prac.19943360806

文献信息

• Stereoselective synthesis of bicyclic lactones by annelation with functionalised orthoesters
  作者：Nuno Maulide、István E. Markó

  DOI：10.1039/b600677a

  日期：——

  An efficient two-step annelation of functionalised orthoesters with trimethylsilyloxyfuran derivatives, which delivers suitably decorated bicyclo[3.n.0]lactones in high overall yields and with complete diastereocontrol of up to three contiguous stereocenters, is reported.

  报告介绍了一种用三甲基硅氧基呋喃衍生物对官能化的原酯进行两步醛化的高效方法，该方法能以较高的总收率提供经适当修饰的双环[3.n.0]内酯，并能完全非对映地控制多达三个连续的立体中心。
• Magnesium bromide promoted Barbier-type intramolecular cyclization of halo-substituted acetals, ketals, and orthoesters
  作者：Jui-Wen Huang、Chiar-Dy Chen、Man-kit Leung

  DOI：10.1016/s0040-4039(99)01813-4

  日期：1999.12

  Although acetals, ketals and orthoesters are commonly used as protective groups against organometallic reagents, Grignard reagents derived from halo-acetals, ketals, or orthoesters cyclize intramolecularly under MgBr2 promoted conditions, giving rise to the corresponding cycloalkanol and cycloalkanone derivatives. Our results also suggest a Lewis acid catalyzed push-pull mechanism operating for the

  尽管缩醛，缩酮和原酸酯通常用作抵抗有机金属试剂的保护基，但是衍生自卤代缩醛，缩酮或原酸酯的格氏试剂在MgBr 2促进的条件下分子内环化，产生了相应的环烷醇和环烷酮衍生物。我们的结果还表明，路易斯酸催化的推挽机制可用于环化反应。
• A new type of carboxypeptidase a inhibitors designed using an imidazole as a zinc coordinating ligand
  作者：Kyung Joo Lee、Keum Chan Joo、Eun-Jung Kim、Mijoon Lee、Dong H Kim

  DOI：10.1016/s0968-0896(97)00134-x

  日期：1997.10

  2-(4-Imidazoyl)hydrocinnamic acid (1) and its congeners (2-4) having different length of alkyl chain spacers between the imidazole ring and the a-carbon to the carboxylate of 1 have been designed, synthesized and evaluated as inhibitors for carboxypeptidase A to show that they are competitive inhibitors for the enzyme. Inhibitor 1 was most potent having the K-i value of 0.8 mu M. The present study demonstrates that imidazole ring is an effective zinc coordinating ligand that can be useful for the design of inhibitors for zinc proteases. (C) 1997 Elsevier Science Ltd.
• Synthese von ?-Acetyl-?-methylenpolyencarbons�ureestern
  作者：Hartmut Laatsch、Alke Pudleiner

  DOI：10.1002/prac.19943360806

  日期：——

  The alpha-methylenpolyene carboxylic acids 1 and 2 are highly active against Gram-positive bacteria. If this activity arises from an interference with the cell membranes, then an abrupt change in biological properties is to be expected with growing chain length of simple model compounds. To make these tests possible, we describe here the synthesis of a series of homologue esters of type 40. Their synthesis was achieved by Wittig reactions of polyene alpha,omega-dialdehydes 6 with acetyl-methylentriphenylphosphoran 5a and the protected carboxymethylmethylen triphenylphosphonium salt 8.
• Thermostable enzymes in organic synthesis, 5. Total synthesis of S-(+)-Z-dodec-3-en-11-olide (ferrulactone II) using a tbadh-generated bifunctional chiron.
  作者：Ehud Keinan、Subhash C. Sinha、Surendra P. Singh

  DOI：10.1016/s0040-4020(01)86469-3

  日期：1991.1

  The total synthesis of (S)-(+)-ferrulactone (2), one of several synergistic aggregation pheromones produced by male flat grain beetles, Cryptolestes ferrugineus (Stephens) was achieved in a five-step synthesis in very high optical purity (>99% ee) and 17.5% chemical yield, starting from (S)-(+)-methyl-8-hydroxynonanoate (5) and a three-carbon Wittig reagent 11. The nine-carbon bifunctional chiron 5

  （S）-（+）-ferrulactone（2）的全合成是雄性扁平甲虫Cryptolestes ferrugineus（Stephens）产生的几种协同聚集信息素之一，是通过五步合成以极高的光学纯度实现的（>从（S）-（+）-甲基-8-羟基壬酸酯（5）和三碳Wittig试剂11开始，获得99％ee）和17.5％的化学收率。通过用布氏嗜热厌氧菌醇脱氢酶（TBADH）对映选择性还原，由8-氧代壬酸甲酯获得九碳双功能Chiron 5。