adlumidinediol | 25344-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: adlumidinediol
• 英文别名: (R)-C'-((R)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-C,C'-benzo[1,3]dioxole-4,5-diyl-bis-methanol；(+)-adlumidinediol；capnoidinediol；(R)-[4-(hydroxymethyl)-1,3-benzodioxol-5-yl]-[(5R)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]methanol
• CAS: 25344-60-9
• 化学式: C₂₀H₂₁NO₆
• 分子量: 371.39
• InChiKey: OYMYKLQFOVFCLR-RTBURBONSA-N

物化性质

• 沸点：
  564.2±50.0 °C(Predicted)
• 密度：
  1.428±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  80.62
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  (1S)-trans-1,5,6,10b-tetrahydro-1-(1,3-benzodioxol-5-yl)-3H-oxazolo<4,3-a>1,3-dioxolo<4,5-g>isoquinolin-3-one 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 22.0h， 生成 adlumidinediol
  参考文献：
  名称：

  Synthesis of the phthalide isoquinoline alkaloids (-)-egenine, (-)-corytensine, and (-)-bicuculline by asymmetric carbonyl addition of chiral dipole-stabilized organometallics

  摘要：

  The asymmetric addition of metalated [(methylenedioxy)isoquinolyl]oxazolines is 100% selective for the erythro (alpha-hydroxybenzyl)isoquinoline diastereomers, with 2:1 selectivity of the two possible erythro stereoisomers. Enrichment to 100% ee after removal of the auxiliary and conversion to (-)-bicuculline and (+)-bicuculline diol establish the absolute configuration of the major addition product. Inversion of the C-9 hydroxyl affords entry into the threo series as well. The asymmetric carbonyl addition was used to synthesize, for the first time, the phthalide-isoquinoline hemiacetals corytensine and egenine, confirming the previously assigned structures and absolute configurations, and establishing the identity of egenine with decumbensine and of corytensine with epi-alpha-decumbensine.

  DOI：

  10.1021/jo00004a041

文献信息

• Alkaloids of Corydalis incisa PERS. V. The structures of corydalispirone and corydalisol.
  作者：GENICHIRO NONAKA、ITSUO NISHIOKA

  DOI：10.1248/cpb.23.294

  日期：——

  Two new alkaloids, corydalispirone, C20H17O6N, mp 196-198°, [α] D 0°, and corydalisol, C20H21O5N, mp 160-161°, [α] D +21.4°, were isolated from Corydalis incisa PERS. (Papaveraceae). The structure of corydalispirone was established to be I by the spectroscopic examinations and chemical correlation with bicucullinediol and adlumidinediol, and the structure of corydalisol was determined as VIII by the conversion to d-tetra-hydrocoptisine. Corydalispirone and corydalisol are noted as a new series of isoquinoline-type alkaloids having one more carbon atom at the benzyl moiety, and probably are metabolites of coptisine.

  从深切紫堇 PERS 中分离出两种新的生物碱，紫堇螺酮，C20H17O6N，熔点 196-198°，[α] D 0°，和紫堇醇，C20H21O5N，熔点 160-161°，[α] D +21.4°。 （罂粟科）。经光谱分析及与荷包牡丹二醇、阿杜脒二醇的化学关联，确定紫堇螺酮的结构为I，经转化为d-四氢黄连碱，确定紫堇醇的结构为VIII。紫堇螺酮和紫堇醇被认为是在苄基部分多一个碳原子的一系列新的异喹啉型生物碱，并且可能是黄连碱的代谢产物。
• ROZWADOWSKA, MARIA D.;MATECKA, DOROTA, LIEBIGS ANN. CHEM.,(1991) N, C. 287-289
  作者：ROZWADOWSKA, MARIA D.、MATECKA, DOROTA

  DOI：——

  日期：——
• REIN, KATHLEEN S.;GAWLEY, ROBERT E., J. ORG. CHEM., 56,(1991) N, C. 1564-1569
  作者：REIN, KATHLEEN S.、GAWLEY, ROBERT E.

  DOI：——

  日期：——