(S)-1-[(S)-oxiran-2-yl]prop-2-en-1-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-[(S)-oxiran-2-yl]prop-2-en-1-ol
• 英文别名: (S)-1-[(S)-oxiran-2-yl]prop-2-enol；(1S)-1-[(2S)-oxiran-2-yl]prop-2-en-1-ol
• 化学式: C₅H₈O₂
• 分子量: 100.117
• InChiKey: YYUNQECXARGEAQ-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-[(S)-oxiran-2-yl]prop-2-en-1-ol 在 咪唑 、 copper(l) iodide 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (3S,4S)-3,4-bis(tert-butyldimethylsiloxy)oct-1-en-7-yne
  参考文献：
  名称：

  Stereocomplementary Construction of Optically Active Bicyclo[4.3.0]nonenone Derivatives

  摘要：

  Treatment of (5S,6S)-5,6-bis(tert-butyldimethylsiloxy)-8-(substituted)oct-1-en-7-yne derivatives, prepared from diethyl L-tartrate, with Co-2(CO)(8) afforded the corresponding cobalt-complexed enynes, which were subsequently exposed to the typical Pauson-Khand conditions to furnish highly stereoselectively or exclusively (2S,3S,6S)-2,3-bis(tert-butyldimetbylsiloxy)-9-(substituted)bicyclo[4.3.0]non-1(9)-en-8-ones. On the other hand, (3S,4S)-1-(substituted)oct-7-en-1-yne-3,4-diol congeners produced, on exposure to the Pauson-Khand conditions, (2S,3S,6R)-2,3-dihydroxy-9-(substituted) bicyclo[4.3.0]-non-1(9)-en-8-one derivatives in a highly stereoselective manner. The newly developed procedure has been shown to be useful for construction of the 2,3-bis(oxygenated)-7-(substituted)-bicyclo[4.3.0]non-6-en-8-one framework in a stereocomplementary as well as stereoselective fashion.

  DOI：

  10.1021/jo990819z
• 作为产物：
  描述：

  ((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 24.17h， 生成 (S)-1-[(S)-oxiran-2-yl]prop-2-en-1-ol
  参考文献：
  名称：

  Stereocomplementary Construction of Optically Active Bicyclo[4.3.0]nonenone Derivatives

  摘要：

  Treatment of (5S,6S)-5,6-bis(tert-butyldimethylsiloxy)-8-(substituted)oct-1-en-7-yne derivatives, prepared from diethyl L-tartrate, with Co-2(CO)(8) afforded the corresponding cobalt-complexed enynes, which were subsequently exposed to the typical Pauson-Khand conditions to furnish highly stereoselectively or exclusively (2S,3S,6S)-2,3-bis(tert-butyldimetbylsiloxy)-9-(substituted)bicyclo[4.3.0]non-1(9)-en-8-ones. On the other hand, (3S,4S)-1-(substituted)oct-7-en-1-yne-3,4-diol congeners produced, on exposure to the Pauson-Khand conditions, (2S,3S,6R)-2,3-dihydroxy-9-(substituted) bicyclo[4.3.0]-non-1(9)-en-8-one derivatives in a highly stereoselective manner. The newly developed procedure has been shown to be useful for construction of the 2,3-bis(oxygenated)-7-(substituted)-bicyclo[4.3.0]non-6-en-8-one framework in a stereocomplementary as well as stereoselective fashion.

  DOI：

  10.1021/jo990819z

文献信息

• Structure and Absolute Stereochemistry of the Anticancer Agent EBC-23 from the Australian Rainforest
  作者：Lin Dong、Victoria A. Gordon、Rebecca L. Grange、Jenny Johns、Peter G. Parsons、Achim Porzelle、Paul Reddell、Heiko Schill、Craig M. Williams

  DOI：10.1021/ja807133p

  日期：2008.11.19

  EBC-23 (2), a prostate anticancer agent, was isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforest. Extensive NOE experiments enabled the relative stereochemistry of the proposed EBC-23 (2) structure to be determined. Total synthesis of both enantiopodes over nine linear steps, involving challenging RCM and spiroacetal cyclizations, confirmed the gross

  EBC-23 (2) 是一种前列腺抗癌剂，是从澳大利亚热带雨林的 Cinnamomum laubatii（樟科）的果实中分离出来的。广泛的 NOE 实验能够确定所提出的 EBC-23 (2) 结构的相对立体化学。通过九个线性步骤对两种对映体进行全合成，包括具有挑战性的 RCM 和螺缩醛环化，证实了总体结构以及相对和绝对立体化学。
• Stereoselective epoxidation of divinylmethanol: A synthetic approach to the pentitols
  作者：David Holland、J. Fraser Stoddart

  DOI：10.1016/s0008-6215(00)81036-8

  日期：——

  -butyl hydroperoxide with catalytically active Ti 4+ , V 5+ , or Mo 6+ complexes are employed as epoxidation reagents. However, the diastereoselectivities characterising the epoxidations and the regioselectivities governing the epoxide-ring openings are not sufficiently high to constitute an attractive synthesis of either ribitol, dl -arabinitol, or xylitol from divinylmethanol.

  摘要二乙烯基甲醇（9）的过氧酸环氧化，然后进行乙酰化，得到具有赤型（53％）和苏型（47％）构型的乙酰化单环氧化物1和2。1和2的过氧酸环氧化产生了乙酰化的二环氧化物3（赤藓红，36％）和4（赤藓红，64％）（来自1）和4（赤藓红，47％）和5（苏绿） -threo，5​​3％）（来自2）。根据（a）1 Hn.mr化学位移和偶合常数数据，对相对构型分配为1-5，（b）观察到1仅给出3和4，而2仅给出4和5 （c）在乙酸酐中带有乙酸根离子的3-5分别在其伯碳原子上优先经历环氧化物开环的事实，分别得到核糖醇，dl-阿拉伯糖醇和木糖醇的五乙酸盐，作为主要产品。当过氧酸或叔丁基氢过氧化物与具有催化活性的Ti 4+，V 5+或Mo 6+配合物用作环氧化试剂时，环氧化物环的形成有利于赤型构型。但是，表征环氧化作用的非对映选择性和控制环氧化物开口的区域选择性不够高，不足以构成由二乙烯基甲醇合成核糖醇，1
• Stereoselective synthesis of protected <scp>l</scp>- and <scp>d</scp>-dideoxysugars and analogues via Prins cyclisations
  作者：Ryan J. Beattie、Thomas W. Hornsby、Gemma Craig、M. Carmen Galan、Christine L. Willis

  DOI：10.1039/c5sc04144a

  日期：——

  Cyclisation of a silicon acetal with homoallylic alcohols to generate silyltetrahydropyrans and subsequent oxidation gives rapid access to deoxyglycoside analogues.

  硅缩醛与高烯丙醇环化生成甲硅烷基四氢吡喃，随后氧化可快速获得脱氧糖苷类似物。
• Anticancer Agents from the Australian Tropical Rainforest: Spiroacetals EBC-23, 24, 25, 72, 73, 75 and 76
  作者：Lin Dong、Heiko Schill、Rebecca L. Grange、Achim Porzelle、Jenny P. Johns、Peter G. Parsons、Victoria A. Gordon、Paul W. Reddell、Craig M. Williams

  DOI：10.1002/chem.200901525

  日期：2009.10.26

  EBC‐23, 24, 25, 72, 73, 75 and 76 were isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforests. EBC‐23 (1) was synthesized stereoselectively, in nine linear steps in 8 % overall yield, to confirm the reported relative stereochemistry and determine the absolute stereochemistry. Key to the total synthesis was a series of Tietze–Smith linchpin reactions

  EBC-23、24、25、72、73、75和76是从澳大利亚热带雨林中的laubatii肉桂（月桂科）的果实中分离出来的。EBC-23（1）以9个线性步骤立体选择性合成，总产率为8％，以确认报道的相对立体化学并确定绝对立体化学。全面合成的关键是一系列的Tietze–Smith linchpin反应。发现新的螺缩醛结构基序，例如EBC-23（1），可在小鼠模型中抑制雄激素非依赖性前列腺肿瘤细胞DU145的生长，表明其具有治疗成人难治性实体瘤的潜力。
• Formal synthesis of <i>cis</i>-solamin: acid-catalyzed one-step construction of 2,5-disubstituted tetrahydrofuran
  作者：Koichiro Ota、Tomoko Yamashita、Sumika Kohno、Atsuko Miura、Kazuo Kamaike、Hiroaki Miyaoka

  DOI：10.1039/c8ob00603b

  日期：——

  strategy has been used for the concise and efficient enantioselective formal synthesis of Annonaceous acetogenin cis-solamin. Our synthetic strategy comprises concise preparation of the diepoxyester via an 11-membered silaketal constructed by ring-closing metathesis after the dimerization of chiral epoxides, and uses an acid-catalyzed tandem intramolecular SN2-like reaction to construct the threo-cis-threo

  已经采用了一种不同的策略来简便，高效地合成Annanoaceous acetogenin顺式-solamin的对映选择性形式。我们的合成策略包括通过手性环氧化物二聚后通过闭环易位而构建的11元硅酮来制备二环氧酯，并使用酸催化的串联分子内S N 2类反应来构建苏式-顺式-苏式四氢呋喃-二醇部分的构型。