1-(10,10-dimethyl-3,3-dioxo-3χ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-2-phenylethane-1,2-dione | 181027-09-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-(10,10-dimethyl-3,3-dioxo-3χ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-2-phenylethane-1,2-dione
• 英文别名: N-phenylglyoxyloyl-(2R)-bornane-10,2-sultam；1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-phenylethane-1,2-dione；1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-phenylethane-1,2-dione
• CAS: 181027-09-8
• 化学式: C₁₈H₂₁NO₄S
• 分子量: 347.435
• InChiKey: QHPKFYVKVCZAHM-HBUWYVDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  79.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(10,10-dimethyl-3,3-dioxo-3χ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-2-phenylethane-1,2-dione 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 15.0h， 生成 (R)-2,3-diphenyl-1,2-propanediol
  参考文献：
  名称：

  Raszplewicz; Sikorska; Kiegiel, Polish Journal of Chemistry, 2005, vol. 79, # 12, p. 1901 - 1907

  摘要：

  DOI：
• 作为产物：
  描述：

  氧代(苯基)乙酰氯 、 (2R)-bornane-10,2-sultam 在 sodium hydride 作用下， 以 甲苯 为溶剂， 以71%的产率得到1-(10,10-dimethyl-3,3-dioxo-3χ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl)-2-phenylethane-1,2-dione
  参考文献：
  名称：

  （2 R）-N-丙酮酰-和（2 R）-N-（苯乙氧基酰）硼烷-10,2-磺胺的高效制备和X射线结构分析†

  摘要：

  报告了两种标题化合物的有效合成及其X射线晶体结构分析。基于立体电子学考虑的讨论使N-酰基冰片烷10,2-磺胺的结晶SO 2 / C（O）顺-平面构象体的第一个例子合理化。

  DOI：

  10.1002/hlca.19960790414

文献信息

• Diastereoselective allylation of α-ketoamides bearing camphor N-tosylpyrazolidinone auxiliary: efficient synthesis of highly optically active two stereoisomers
  作者：Jung-Hsuan Chen、Uppala Venkatesham、Li-Chen Lee、Kwunmin Chen

  DOI：10.1016/j.tet.2005.10.042

  日期：2006.1

  Complementary allylation conditions were developed for the synthesis of both diastereomers of tertiary homoallylic alcohols. Treatment of camphor N-tosylpyrazolidinone derived α-ketoamides with allyltributylstannane afforded both the individual homoallylic alcohols in high optical purity (up to 98% de) when the reaction was carried out in the presence of Sn(OTf)2 and PdCl2, respectively. The stereochemical

  开发了互补的烯丙基化条件以合成叔均烯丙基醇的两种非对映异构体。当反应分别在Sn（OTf）2和PdCl 2的存在下进行时，用烯丙基三丁基锡烷处理樟脑N-甲苯磺酰基吡唑烷酮衍生的α-酮酰胺可提供高光学纯度（最高98％de）的两种均烯丙基醇。基于13 C NMR和FTIR研究，提出了反应中的立体化学结果和立体选择性的逆转。
• Indium-mediated diastereoselective allylation reactions: preparation of tert-α-hydroxy acids
  作者：Jeong Ah Shin、Joo Hwan Cha、Ae Nim Pae、Kyung Il Choi、Hun Yeong Koh、Han-Young Kang、Yong Seo Cho

  DOI：10.1016/s0040-4039(01)01064-4

  日期：2001.8

  Indium-mediated allylation reactions of α-ketoimides derived from Oppolzer's sultam were accomplished in aqueous THF in good yields and excellent diastereomeric excesses. It could be a useful method for the preparation of enantiopure t-α-hydroxy acids. When the substituent of α-ketoimides was changed from phenyl to thiophenyl or furyl group, diastereoselectivity decreased in comparison to N-phenyl

  由Oppolzer's sultam衍生的α-酮亚胺的铟介导的烯丙基化反应可在THF水溶液中以良好的收率和出色的非对映异构体过量进行。这可能是制备对映纯t -α-羟基酸的有用方法。当α-酮酰亚胺的取代基从苯基变为硫代苯基或呋喃基时，与N-苯基衍生物相比，非对映选择性降低，但将溶剂变为乙醇水溶液则提高了非对映选择性。
• Diastereoselective addition of allylic reagents to chiral α-ketoimides derived from Oppolzer's sultam
  作者：Katarzyna Kiegiel、Janusz Jurczak

  DOI：10.1016/s0040-4039(98)02470-8

  日期：1999.1

  Additions of allylmagnesium chloride and allyl bromide in the presence of zinc dust to N-methyl- and N-phenylglyoxyloyl-(2R)-bornane-10,2-sultam and the Lewis acid-mediated additions of allyltrimethylsilane to these chiral α-ketoimides were studied. High diastereoselection in these reactions was observed, and in the case of the allyltrimethylsilane/TiCl4 additions, a change of direction of asymmetric

  在存在锌粉的情况下，将烯丙基氯化镁和烯丙基溴添加到N-甲基和N-苯基乙氧基乙酰-（2 R）-降冰片烷10,2-sultam中，以及路易斯酸介导的将烯丙基三甲基硅烷添加到这些手性α-酮亚胺中被研究了。在这些反应中观察到高非对映选择性，并且在添加烯丙基三甲基硅烷/ TiCl 4的情况下，发现不对称诱导的方向改变。
• Highly diastereoselective allylation and reduction of chiral camphor-derived α-ketoamides
  作者：Neelesh A. Kulkarni、Shy-Guey Wang、Li-Chen Lee、Huei Ru Tsai、Uppala Venkatesham、Kwunmin Chen

  DOI：10.1016/j.tetasy.2006.01.011

  日期：2006.2

  The diastercoselective allylation and reduction of camphor-derivcd alpha-ketoamides to give optically enriched a-hydroxyl amides with high to excellent stereoselectivities are described. Allylation was carried out using allyltributylstannane in the presence of a stoichiometric amount of a Lewis acid to afford the desired homoallylic alcohols in relatively high chemical yields (up to 98%) and stereoselectivities (LIP to 98% de). Diastereoselective reductions were performed with the relatively bulky hydride K-Selectride at -78 degrees C to give the corresponding a-hydroxy amides in excellent chemical yields (LIP to 98%) and stereoselectivities (up to 98% de). The absolute configuration of the new stereogenic center of the major diastereomer was established by X-ray crystallographic analysis. Finally, stereochemical induction and the Lewis acid dependent reversal of stereoselectivity is described. (c) 2006 Elsevier Ltd. All rights reserved.
• Asymmetric Hetero-Diels-Alder Addition of 1-Methoxybuta-1,3-diene to (2R)-N-Pyruvoyl- and (2R)-N-(Phenylglyoxyloyl)bornane-10,2-sultam
  作者：Jaroslaw Kiegiel、Christian Chapuis、Zofia Urbañczyk-Lipkowska、Janusz Jurczak

  DOI：10.1002/(sici)1522-2675(19980909)81:9<1672::aid-hlca1672>3.0.co;2-0

  日期：1998.9.9