dihydroarteannuin B | 64390-16-5

• 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: dihydroarteannuin B
• 英文别名: 3-S-dihydroarteannuin B；(1R,4S,5S,8R,9S,12R,14R)-4,8,12-trimethyl-2,13-dioxatetracyclo[7.5.0.01,5.012,14]tetradecan-3-one
• CAS: 64390-16-5
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: VWGPQZZLIAQJCE-DWIPZSBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dihydroarteannuin B 在 氢氧化钾 、 三氟化硼乙醚 、 乙酸酐 、 二甲基亚砜 作用下， 反应 5.0h， 生成 (3S,3aS,6aS,9R,10aS)-3,6,9-trimethyl-3a,4,6a,7,8,9-hexahydro-3H-benzo[h][1]benzofuran-2,10-dione
  参考文献：
  名称：

  三氟化硼乙酸酐催化的二氢青蒿素B重排

  摘要：

  二氢青蒿素B与三氟化硼-乙酸酐反应的化合物为主要产物，其结构已通过化学转化，光谱数据确定，并最终通过X射线分析证实。

  DOI：

  10.1016/s0040-4020(97)01049-1
• 作为产物：
  描述：

  青蒿素 B 在 甲醇 、 水 、 magnesium 、 cadmium(II) chloride 作用下， 反应 0.5h， 生成 dihydroarteannuin B
  参考文献：
  名称：

  Selective Reduction of the Exomethylene Group of α-Methylene γ- or δ-Lactones with CdCl2–Mg–MeOH–H2O‡

  摘要：

  倍半萜类化合物中δ-亚甲基δ-或δ-内酯分子的受约束外亚甲基可以用 CdCl2âMgâMeOHâH2O 试剂体系进行选择性还原。

  DOI：

  10.1039/a803981j

文献信息

• Synthesis of (+)-artemisinin and (+)-deoxoartemisinin from arteannuin B and arteannuic acid
  作者：Deanne M Nowak、Peter T Lansbury

  DOI：10.1016/s0040-4020(97)10286-1

  日期：1998.1

  (+)-Artemisinin and (+)-Deoxoartemisinin were prepared for the first time from arteannuin B. The synthetic route is short and efficient, making use of the prior art for the final photo-oxygenation/cyclization reaction. A convergent route to each of the above-named products from arteannuic acid is also described. A novel oxidative lactonization reaction was developed for this sequence.

  由青蒿素B首次制备了（+）-青蒿素和（+）-脱氧青蒿素。合成路线短而有效，利用现有技术进行最终的光氧合/环化反应。还描述了从青蒿酸到上述每种产物的收敛途径。为此序列开发了一种新型的氧化内酯化反应。
• Selective Reduction of the Exomethylene Group of α-Methylene γ- or δ-Lactones with CdCl2–Mg–MeOH–H2O‡
  作者：Asish K. Bhattacharya、Dharam C. Jain、Ram P. Sharma

  DOI：10.1039/a803981j

  日期：——

  The strained exomethylene group of the α-methylene γ- or δ-lactone moiety in sesquiterpenoids can be selectively reduced with the CdCl2–Mg–MeOH–H2O reagent system.

  倍半萜类化合物中δ-亚甲基δ-或δ-内酯分子的受约束外亚甲基可以用 CdCl2âMgâMeOHâH2O 试剂体系进行选择性还原。
• Stereoselective reduction of arteannuin B and its chemical transformations
  作者：Asish K Bhattacharya、Mahesh Pal、Dharam C Jain、Bhawani S Joshi、Raja Roy、Urszula Rychlewska、Ram P Sharma

  DOI：10.1016/s0040-4020(03)00330-2

  日期：2003.4

  Absolute stereochemistry of dihydroarteannuin B 5 obtained by the reduction of arteannuin B 3 with Ni2B, NaBH4 or CdCl2-Mg-MeOH-H2O has been established by 2D NMR and single crystal X-ray diffraction studies. Some experiments aimed at the synthesis of dihydrodeoxyarteannuin B [C-4, 5 double bond isomer of 11] are also discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.
• [EN] METHOD FOR EXTRACTING ARTEMISIA ANNUA HAVING EXCELLENT MEDICINAL PROPERTIES AND METHOD FOR PREPARING HEALTH SUPPLEMENT FOOD WITH MAXIMIZED TASTE AND MEDICINAL EFFICACY USING ARTEMISIA ANNUA EXTRACT<br/>[FR] PROCÉDÉ D'EXTRACTION D'ARTEMISIA ANNUA PRÉSENTANT D'EXCELLENTES PROPRIÉTÉS MÉDICINALES ET PROCÉDÉ DE PRÉPARATION D'UN COMPLÉMENT ALIMENTAIRE DE SANTÉ POSSÉDANT UN GOÛT ET UNE EFFICACITÉ MÉDICINALE MAXIMISÉS À L'AIDE D'UN EXTRAIT D'ARTEMISIA ANNUA<br/>[KO] 약효성분이 우수한 개똥쑥 추출방법과 개똥쑥 추출물을 이용한 맛과 약효를 극대화한 건강보조식품제조방법
  申请人：PARK SEO YEONG

  公开号：WO2020122397A1

  公开（公告）日：2020-06-18

  본 발명은 개똥쑥에 함유되어 있는 기름성분을 추출기에서 제거하고, 개똥쑥이 함유하고 있는 성분을 1차로 추출하기 위하여 100-110℃로 가열하고 냉각되는 순환에 의해 추출물을 얻은 후 2차 100-110℃로 가열하고 냉각하는 순환작업으로 개똥쑥에 잔류로 남아있는 성분을 추출한 다음 다시 저온 60-90℃에서 증류시켜 2차추출물을 추출한 후 1차추출물과 2차 추출물을 혼합한 개똥쑥 추출물을 사용하여 약효를 극대화하고, 인삼분말, 백봉령뿌리가루, 생지황즙, 구기자열매가루를 1: 3: 10.5: 2의 비율로 교반하여 혼합하는 혼합물을 5-6일간 저온 숙성시켜 숙성된 혼합물과 개똥쑥 추출물을 혼합하여 맛이 월등하고 약효가 뛰어난 건강보조식품을 제공하는 데 그 목적이 있는 것이다.
• Boron trifluoride-acetic anhydride catalysed rearrangement of dihydroarteannuin B
  作者：Asish K Bhattacharya、Dharam C Jain、Ram P Sharma、Raja Roy、Andrew T McPhail

  DOI：10.1016/s0040-4020(97)01049-1

  日期：1997.11

  The reaction of dihydroarteannuin B with boron trifluoride-acetic anhydride furnished compound as the major product whose structure has been established by chemical transformations, spectral data and finally confirmed by x-ray analysis.

  二氢青蒿素B与三氟化硼-乙酸酐反应的化合物为主要产物，其结构已通过化学转化，光谱数据确定，并最终通过X射线分析证实。