(2R,3R,4R)-2,3-dihydroxy-4-octylbutyrolactone | 133710-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R)-2,3-dihydroxy-4-octylbutyrolactone
• 英文别名: (2R,3S,4R)-2,3-dihydroxy-4-octylbutyrolactone；(3R,4R,5R)-3,4-dihydroxy-5-octyloxolan-2-one
• CAS: 133710-19-7
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: DOSDLHXXVXFXCY-OUAUKWLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-2,3-dihydroxy-4-octylbutyrolactone 在 咪唑 、 tri-iodoimidazole 、 三苯基膦 、 锌 作用下， 以 甲苯 为溶剂， 以72%的产率得到5-辛基-5H-呋喃-2-酮
  参考文献：
  名称：

  Yoda, Hidemi; Shirakawa, Koji; Takabe, Kunihiko, Chemistry Letters, 1991, # 3, p. 489 - 490

  摘要：

  DOI：
• 作为产物：
  描述：

  正辛基镁溴盐 在 盐酸 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 为溶剂， 生成 (2R,3R,4R)-2,3-dihydroxy-4-octylbutyrolactone
  参考文献：
  名称：

  Yoda, Hidemi; Shirakawa, Koji; Takabe, Kunihiko, Chemistry Letters, 1991, # 3, p. 489 - 490

  摘要：

  DOI：

文献信息

• Chiral cyclic imides with c2-symmetry. Novel reagents for the synthesis of optically pure lactones containing three contiguous tertiary centers
  作者：Hidemi Yoda、Koji Shirakawa、Kunihiko Takabe

  DOI：10.1016/s0040-4039(00)92719-9

  日期：1991.7

  Asymmetric reactions employing C2-symmetrical imides readily prepared from L-tartaric acid with Grignard reagents and sodium borohydride afforded a separable mixture of two hydroxyamides with high diastereoselectivity. Products were lactonized respectively to provide optically pure γ- alkylated lactones with contiguous tertiary carbon centers. The reaction mechanisms in asymmetric induction were also

  使用由L-酒石酸与Grignard试剂和氢硼化钠轻松制备的C 2-对称酰亚胺进行的不对称反应提供了具有高非对映选择性的两种羟酰胺的可分离混合物。将产物分别内酯化以提供具有连续的叔碳中心的光学纯的γ-烷基化内酯。还讨论了不对称诱导中的反应机理。
• Stereoselective syntheses of γ-alkyl (aryl)-α,β-dihydroxy-γ-butyrolactones and naturally occurring lipid guggultetrol
  作者：Kavirayani R. Prasad、Appayee Chandrakumar

  DOI：10.1016/j.tet.2006.12.037

  日期：2007.2

  gamma-Oxo-butyramides derived from tartaric acid serve as excellent precursors for the synthesis of gamma-alkyl (aryl)-alpha,beta-dihydroxy-gamma-butyrolactones and for the synthesis of tetrols containing three contiguous stereogenic centres. The methodology presented here is general for the synthesis of gamma-alkyl (aryl)-alpha,beta-dihydroxy-gamma-butyrolactones. Utility of the chiral building block was demonstrated by the synthesis of naturally occurring lipid guggultetrol. (c) 2006 Elsevier Ltd. All rights reserved.
• Optically Pure Dihydroxy γ-Alkylated γ-Butyrolactones Starting from <scp>l</scp>-Tartaric Acid:  Application to Formal and Total Syntheses of Natural Products
  作者：Anne-Marie Fernandez、Jean-Christophe Plaquevent、Lucette Duhamel

  DOI：10.1021/jo970117e

  日期：1997.6.13

  A general and efficient preparation of epimeric optically pure gamma-butyrolactones 2 and 3 is described starting from L-tartaric acid (1). These lactones are well-known to be important building blocks in the syntheses of natural products. L-Tartaric acid (1) was transformed into carbonylated chirons (ketones 4 and aldehyde 5). These chirons, when submitted to highly stereoselective reactions (reduction or organometallic addition), led to epimeric dihydroxy gamma-butyrolactones 2 and 3 after lactonization and deprotection steps. The resulting optically pure lactones are precursors of biological compounds and have allowed a total synthesis of L-biopterin and formal syntheses of quercus lactone, dodecanolactone, avenaciolide, and tetrahydrocerulenin.
• Yoda, Hidemi; Shirakawa, Koji; Takabe, Kunihiko, Chemistry Letters, 1991, # 3, p. 489 - 490
  作者：Yoda, Hidemi、Shirakawa, Koji、Takabe, Kunihiko

  DOI：——

  日期：——