(S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentan-1-ol | 87604-44-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentan-1-ol
• 英文别名: (1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]pentan-1-ol
• CAS: 87604-44-2
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: LDMLFIWGAGIHFD-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentan-1-ol 、 吡啶 、 甲醇 生成 (1S)-1-[(2R)-oxiran-2-yl]pentan-1-ol
  参考文献：
  名称：

  SATO, FUMIE;KOBAYASHI, YUICHI;TAKAHASHI, OSAMU;CHIBA, TSUNEHISA;TAKEDA, Y+, J. CHEM. SOC. CHEM. COMMUN., 1985, N 22, 1636-1638

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R)-1,2-O-isopropylidene-3-oxoheptan-1,2-diol 生成 (S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentan-1-ol
  参考文献：
  名称：

  CHIKASHITA, HIDENORI;NIKAYA, TOSHIKI;UEMURA, HIROMITSU;ITOH, KAZUYOSHI, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 2121-2123

  摘要：

  DOI：

文献信息

• Stereoselective addition of organomanganese reagents to chiral acylsilanes and aldehydes
  作者：Céline Boucley、Gérard Cahiez、Silvia Carini、Vanda Cerè、Mauro Comes-Franchini、Paul Knochel、Salvatore Pollicino、Alfredo Ricci

  DOI：10.1016/s0022-328x(00)00902-5

  日期：2001.4

  Organomanganese halides and organomanganates prepared by transmetalation of organolithium and Grignard reagents add smoothly to the carbonyl moiety of acylsilanes and of substituted aldehydes bearing a chiral center at the α-position affording the desired alcohols in good to excellent yields and with essentially no undesired products from enolization. Comparison of the stereochemical outcome with that

  通过有机锂和格氏试剂的金属转移而制备的有机锰卤化物和有机锰酸盐可平滑地添加到酰基硅烷和取代醛的羰基部分上，该醛在α-位带有手性中心，可提供所需醇，收率良好至极佳，并且基本上没有烯醇化产生的不良产物。将立体化学结果与其他有机金属物种所观察到的结果进行了比较，概述了有机锰试剂诱导均一的良好非对映选择性的能力，在许多情况下，其显着高于先前对这些反应的报道。在酰基硅烷12的比较中清楚地显示了R 3 Si基团在促进高1,2-不对称感应中所发挥的关键作用。与相应的醛13。Cram /抗Cram选择性的含义取决于参与这些反应的羰基试剂的性质。
• On the steric course of the addition of some organometallic reagents to (R)-2,3-isopropylidene glyceraldehyde. Synthesis of optically active α-benzyloxy aldehydes, alcohols, carboxylic acids and 1,2-diols.
  作者：Johann Mulzer、Alfred Angermann

  DOI：10.1016/s0040-4039(00)88039-9

  日期：1983.1

  Organo-titanium and organo-zinc reagents were added stereoselectively to (R)-2,3-isopropylidene glyceraldehyde (1) to give the alcohols 23, which were converted into the optically active derivatives 4–11.

  将有机钛和有机锌试剂立体选择性地添加到（R）-2,3-异亚丙基甘油醛（1）中，得到醇23，将其转化为旋光性衍生物4-11。
• Synthesis of the rarely obtained syn-adducts in the reaction of organocopper compounds with 2,3-O-isopropylideneglyceraldehyde. Preparation of optically active epoxy alcohols
  作者：Fumie Sato、Yuichi Kobayashi、Osamu Takahashi、Tsunehisa Chiba、Yoshiyuki Takeda、Masato Kusakabe

  DOI：10.1039/c39850001636

  日期：——

  Organocopper compounds, prepared from Grignard reagents and copper(I) iodide in tetrahydrofuran-dimethyl sulphide, react with 2,3-O-isopropylideneglyceraldehyde highly stereoselectively (>10:1) affording the rarely obtained syn-addition products which can be readily converted into optically active epoxy alcohols, useful intermediates in organic synthesis.

  由格氏试剂和碘化亚铜（I）在四氢呋喃-二甲基硫醚中制备的有机铜化合物与2,3- O-异亚丙基甘油醛高度立体选择性（> 10：1）反应，提供了很少获得的合成加成产物，可以轻松地将其转化为旋光性环氧醇，在有机合成中有用的中间体。
• Stereoselective<i>syn</i>-Reduction of (<i>R</i>)-4-Acyl-2,2-dimethyl-1,3-dioxolanes with Metal Hydride Reagents
  作者：Hidenori Chikashita、Toshiki Nikaya、Hiromitsu Uemura、Kazuyoshi Itoh

  DOI：10.1246/bcsj.62.2121

  日期：1989.6

  Lithium tri-s-butylborohydride and lithium aluminum hydride were found to be efficient reducing agents for the stereoselective preparation of syn-glycerol derivatives from (R)-4-acyl-2,2-dimethyl-1,3-dioxolanes. The scope and limitation of the stereoselective L-Selectride reduction of (R)-4-acyl-2,2-dimethyl-1,3-dioxolanes were also described.

  发现三叔丁基硼氢化锂和氢化铝锂是从 (R)-4-酰基-2,2-二甲基-1,3-二氧戊环立体选择性制备合成甘油衍生物的有效还原剂。还描述了 (R)-4-酰基-2,2-二甲基-1,3-二氧戊环的立体选择性 L-Selectride 还原的范围和限制。
• A Study of the Influence of Base, Temperature and Reaction Time in Nitroaldol Reactions Using (R)-(+)-Glyceraldehyde Acetonide: Diastereoselective Synthesis of (4R, 5R)-Dihydro-5-((R)-1,2-Dihydroxyethyl)-4-Nitrofuran- 2(3H)-one
  作者：Erica Pennaforte、Jeronimo Costa、Cristiane Silva、Marcelo Saraiva、Vera Pereira

  DOI：10.2174/157017809787582771

  日期：2009.3.1

  The Henry reaction between the nitroalkanes 6-11 and (R)-(+)-glyceraldehyde acetonide (1), was investigated in respect to the variation of the base, temperature and reaction time. Nitroalcohols 5a-f were obtained in good yields (70- 85%) and moderate to good anti-selectivities (50-79%). The transformation of the nitroalcohol 5a,b in title γ-lactone 2, a potential precursor of bioactive β-aminoacids, was also investigated.

  研究了硝基烷烃 6-11 与(R)-(+)-甘油醛缩丙酮（1）之间的亨利反应在碱、温度和反应时间方面的变化。得到的硝基醇 5a-f 产率良好（70-85%），反选择性中等至良好（50-79%）。此外，还研究了硝基醇 5a,b 向标题 γ-内酯 2（一种具有生物活性的 β-氨基酸的潜在前体）的转化。