(3aR,5aS,5bR,8aR,9aR)-7,7-Dimethyl-3a,4,5a,5b,8a,9a-hexahydro-3H-2,5,6,8,9-pentaoxa-1-aza-cyclopenta[b]-as-indacene | 184377-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (3aR,5aS,5bR,8aR,9aR)-7,7-Dimethyl-3a,4,5a,5b,8a,9a-hexahydro-3H-2,5,6,8,9-pentaoxa-1-aza-cyclopenta[b]-as-indacene
• 英文别名: (1R,6R,9S,10R,14R)-12,12-dimethyl-4,8,11,13,15-pentaoxa-3-azatetracyclo[7.6.0.02,6.010,14]pentadec-2-ene
• CAS: 184377-85-3
• 化学式: C₁₁H₁₅NO₅
• 分子量: 241.244
• InChiKey: LVRYYLXFEUPCTQ-SVFDORGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  58.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,5aS,5bR,8aR,9aR)-7,7-Dimethyl-3a,4,5a,5b,8a,9a-hexahydro-3H-2,5,6,8,9-pentaoxa-1-aza-cyclopenta[b]-as-indacene 在 吡啶 、 盐酸 、 sodium hydroxide 、 sodium hypochlorite 、 盐酸羟胺 、 四丁基溴化铵 、 对甲苯磺酸 、 三乙胺 、 三氟乙酸 、 calcium carbonate 、 mercury dichloride 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 110.0h， 生成 (1S,2S,7R,10R,15R)-2-phenylmethoxy-5,9,13,17-tetraoxa-4,12-diazatetracyclo[8.7.0.03,7.011,15]heptadeca-3,11-diene
  参考文献：
  名称：

  Synthesis of chiral oxepinopyran and oxepinooxepane systems from 1,2-isopropylidene furanoside ring-fused cyclic ether derivatives through 4-O-allyl nitrone and nitrile oxide cycloadditions

  摘要：

  A novel strategy was developed by which chiral oxepinopyran and oxepinooxepane derivatives were synthesised from 1,2-isopropylidene furanoside fused pyran and oxepane derivatives by the cycloaddition of 4-O-allyl nitrone or nitrile oxide species generated from the furanoside ring. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01802-5
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 吡啶 、 sodium hypochlorite 、 sodium periodate 、 盐酸羟胺 、 四丁基溴化铵 、 水 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成 (3aR,5aS,5bR,8aR,9aR)-7,7-Dimethyl-3a,4,5a,5b,8a,9a-hexahydro-3H-2,5,6,8,9-pentaoxa-1-aza-cyclopenta[b]-as-indacene
  参考文献：
  名称：

  通过一氧化氮环加成合成大环共轭ψ-二糖：烯基链长控制单糖形成的二氧杂杂环的空前形成

  摘要：

  从碳水化合物衍生的肟合成了各种对称和不对称的异恶唑啉体现的手性大杂环。我们的结果表明，环加成的方式取决于糖部分的烯基链中存在的长度和系链。因此，在某些情况下，可以高选择性地观察到一氧化氮的分子间和分子内环加成。环加合物包含两个通过大环连接的糖单元，因此将其视为假二糖。通过2D-NMR技术和X射线晶体学研究确定了新形成的手性中心的立体化学。

  DOI：

  10.1016/j.tet.2017.04.044

文献信息

• Synthesis of chiral pyranocyclohexane, oxepanocyclohexane, and furylpyran and -oxepane systems by the application of intramolecular nitrone and nitrile oxide cycloaddition of carbohydrate derivatives
  作者：Arani Pal、Ashoke Bhattacharjee、Anup Bhattacharjya、Amarendra Patra

  DOI：10.1016/s0040-4020(99)00105-2

  日期：1999.3

  2-isopropylidene-3-O-cyclohexenyl carbohydrate aldehyde 4 via intramolecular nitrile oxide cycloaddition, and were converted to 2-(2′-tetrahydrofuryl)pyran 28, which incorporates the lasalocid skeleton, and the related oxepane derivative 32 respectively, through modification of the furanoside ring by applying 2-O-allyl carbohydrate nitrone cycloaddition.

  手性非外消旋吡喃环己烷7和8以及氧庚环环己烷11和12通过分子内一氧化氮环加成反应从单个1,2-异亚丙基-3 - O-环己烯基碳水化合物醛4中获得，并转化为2-（2'-四氢呋喃基）吡喃28，通过应用2- O-烯丙基碳水化合物硝酮环加成对呋喃糖苷环的修饰，分别结合了拉索洛西德骨架和相关的环氧庚烷衍生物32。
• Asymmetric epoxidation catalyzed by d-glucose-derived uloses
  作者：Tony K.M Shing、Gulice Y.C Leung

  DOI：10.1016/s0040-4020(02)00577-x

  日期：2002.9

  Three ulose catalysts (1-3) were prepared from D-glucose via an intramolecular nitrile oxide cycloaddition (INOC) as the key step. The enantioselectivity of ulose 2 and 3 in asymmetric epoxidation was poor (up to 26% ee). Ulose 1 afforded good chemical yields (up to 83% yield) and the enantiomeric excess is up to 71% for the formation of (-)-trans-stilbene oxide. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Mukhopadhyay, Ranjan; Datta, Seema; Chattopadhyay, Partha, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 11, p. 1190 - 1193
  作者：Mukhopadhyay, Ranjan、Datta, Seema、Chattopadhyay, Partha、Bhattacharjya, Anup、Patra, Amarendra

  DOI：——

  日期：——
• Synthesis of macrocyclic conjugated ψ-disacharides via nitrile oxide cycloaddition: Alkenyl chain length controlled unprecedented formation of di-oxa heterocycles from monosaccharides
  作者：Jewel Hossain、Ramalingam Natarajan、Ashish K. Banerjee、Swapan Majumdar

  DOI：10.1016/j.tet.2017.04.044

  日期：2017.6

  chiral macroheterocycles were synthesized from carbohydrate derived oximes. Our result shows that the mode of cycloaddition is dependent on the length and tether present in alkenyl chain of sugar moiety. Thus in some cases inter- and intramolecular cycloaddition of nitrile oxide were observed with high selectivity. The cycloadducts contains two sugar units linked via macrocycles thus they are considered

  从碳水化合物衍生的肟合成了各种对称和不对称的异恶唑啉体现的手性大杂环。我们的结果表明，环加成的方式取决于糖部分的烯基链中存在的长度和系链。因此，在某些情况下，可以高选择性地观察到一氧化氮的分子间和分子内环加成。环加合物包含两个通过大环连接的糖单元，因此将其视为假二糖。通过2D-NMR技术和X射线晶体学研究确定了新形成的手性中心的立体化学。
• Synthesis of chiral oxepinopyran and oxepinooxepane systems from 1,2-isopropylidene furanoside ring-fused cyclic ether derivatives through 4-O-allyl nitrone and nitrile oxide cycloadditions
  作者：Arani Pal、Anup Bhattacharjya、Ranjan Mukhopadhyay

  DOI：10.1016/s0040-4039(00)01802-5

  日期：2000.12

  A novel strategy was developed by which chiral oxepinopyran and oxepinooxepane derivatives were synthesised from 1,2-isopropylidene furanoside fused pyran and oxepane derivatives by the cycloaddition of 4-O-allyl nitrone or nitrile oxide species generated from the furanoside ring. (C) 2000 Elsevier Science Ltd. All rights reserved.