5-(bromomethyl)-3-isopropyldihydrofuran-2(3H)-one | 324763-43-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5-(bromomethyl)-3-isopropyldihydrofuran-2(3H)-one
• 英文别名: (3S,5S)-5-Bromomethyl-3-isopropyl-dihydro-furan-2-one
• CAS: 324763-43-1
• 化学式: C₈H₁₃BrO₂
• 分子量: 221.094
• InChiKey: UTRZPUTWVUEKIF-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-(bromomethyl)-3-isopropyldihydrofuran-2(3H)-one 在 sodium periodate 、 四氧化锇 、 水 、 锌 作用下， 以 四氢呋喃 、 水 、 异丙醇 为溶剂， 反应 5.0h， 生成 (2S)-3-methyl-2-(2-oxoethyl)butanoic acid
  参考文献：
  名称：

  The Power of Visual Imagery in Synthesis Planning. Stereocontrolled Approaches to CGP-60536B, a Potent Renin Inhibitor

  摘要：

  Two strategies were developed toward the stereocontrolled synthesis of 8-aryl-3-hydroxy-4-amino2,7-diisopropyloctanoic acids with predetermined stereogenic centers. This is a generic motif in a new class of potent inhibitors of the enzyme renin, exemplified by CGP-60536B. The synthesis relies on the utilization of L-pyroglutamic acid as chiron, and proceeds through the incorporation of required functionality by exploiting internal induction. One of the strategies shows the power of visual imagery in synthesis planning, akin to a Dali-like representation of objects that can be viewed in more than one way. Thus, the entire carbon skeleton of the target molecule is encompassed in a partially functionalized bicyclic indolizidinone precursor. In a second strategy, an intermediate common to the first approach is elaborated into an appended gamma-lactone which is alkylated through enolate chemistry and ultimately transformed into the intended target compound. X-ray crystallography was used to corroborate the structures and stereochemistries of several intermediates.

  DOI：

  10.1021/jo011184i
• 作为产物：
  描述：

  N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-3-N-dimethylbutyramide 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 生成 5-(bromomethyl)-3-isopropyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  肾素抑制剂CGP60536B的融合合成

  摘要：

  伪麻黄碱在新型口服活性肾素抑制剂CGP60536B的合成中作为双重手性辅助和保护基。

  DOI：

  10.1016/s0040-4039(00)01760-3

文献信息

• Oxidative oxygen-nucleophilic bromo-cyclization of alkenyl carbonyl compounds without organic wastes using alkali metal reagents in green solvent
  作者：Katsuhiko Moriyama、Chihiro Nishinohara、Toru Sugiue、Hideo Togo

  DOI：10.1039/c5ra19851h

  日期：——

  developed via the oxidative umpolung of bromide using alkali metal bromide and inorganic oxidant to provide the corresponding cyclization products in high yields. In particular, the use of AcOEt, the solvent of choice for green sustainable reactions, led to the high reactivities of the present reactions. This methodology is highly recommended for green sustainable chemistry because it uses stable and non-hazardous

  通过使用碱金属溴化物和无机氧化剂，通过溴化物的氧化反应，开发了烯基羧酸的溴内酯化和作为氧亲核性溴环化反应的N-烯丙基酰胺的溴环化反应，从而高收率地提供了相应的环化产物。特别地，使用AcOEt，绿色可持续反应的首选溶剂，导致了本反应的高反应性。强烈建议将此方法用于绿色可持续化学，因为它使用稳定且无害的试剂代替其他溴试剂和氧化剂，并且不会产生污染环境的有机废物。
• Divergent Synthesis of α,γ-Disubstituted γ-Butyrolactones through Diastereoselective Bromolactonization with Alkali Metal Bromide: Asymmetric Total Synthesis of (+)-Dubiusamine C
  作者：Katsuhiko Moriyama、Toru Sugiue、Chihiro Nishinohara、Hideo Togo

  DOI：10.1021/acs.joc.5b01497

  日期：2015.9.18

  diastereoselective bromolactonization of α-substituted 4-pentenoic acids and 4-pentenamides via umpolung of bromide by use of alkali metal bromide and Oxone (potassium peroxymonosulfate mixture, 2KHSO5·KHSO4·K2SO4) to obtain mainly cis-products from α-substituted 4-pentenoic acids and trans-products from α-substituted 4-pentenamides, and it was found that the bromonium species generated from KBr and Oxone had higher

  已开发出发散的α-取代的溴甲基γ-内酯合成方法，该方法涉及通过使用碱金属溴化物和Oxone（过氧化一硫酸钾混合物2KHSO 5 ·KHSO 4 ·K 2 SO 4）主要由α-取代的4-戊烯酸获得顺式产物，由α-取代的4-戊烯酰胺获得反式产物，发现由KBr和Oxone生成的溴物种具有更高的活性比N-溴代琥珀酰亚胺大。此外，从中分离出作为次要非对映异构体的（+）-二丁胺C的不对称全合成。露兜树（Pandanus dubius）是通过（S）-α-甲基-4-戊烯酸的顺式-选择性溴化内酯法在9个线性步骤中首次完成的，总收率为36％。