白苏烯酮 | 59204-74-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 白苏烯酮
• 英文名称: egomaketone
• 英文别名: 1-furan-3-yl-4-methyl-pent-3-en-1-one；Egomaketon；1-(furan-3-yl)-4-methylpent-3-en-1-one
• CAS: 59204-74-9
• 化学式: C₁₀H₁₂O₂
• mdl: MFCD01729543
• 分子量: 164.204
• InChiKey: MGIXHQSSTZKVOO-UHFFFAOYSA-N

物化性质

• LogP：
  2.001 (est)
• 物理描述：
  Liquid
• 熔点：
  17°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

毒理性

• 非人类毒性摘录

毒性研究表明，薄荷醇、薄荷酮和异薄荷酮的IP LD50值大致相等，并且在实验室小鼠中产生相同的肺部效果。肺部大体病变与4-异丙醇引起的疾病无法区分；然而，与4-异丙醇不同，薄荷醇不影响成年雄性小鼠的肾脏。/薄荷醇/

TOXICITY STUDIES INDICATE THAT PERILLA KETONE, EGOMAKETONE, & ISOEGOMAKETONE ARE APPROXIMATELY EQUAL IN IP LD50 VALUES & PRODUCE IDENTICAL PULMONARY EFFECTS IN LABORATORY MICE. GROSS PULMONARY LESIONS ARE INDISTINGUISHABLE FROM THE DISEASE CAUSED BY 4-IPOMEANOL; HOWEVER, UNLIKE 4-IPOMEANOL, PERILLA KETONE DOES NOT AFFECT THE KIDNEYS OF ADULT MALE MICE. /PERILLA KETONE/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

3毫克/千克和9毫克/千克的白苏酮分别直接注入瘤胃，安格斯小母牛没有反应。然而，另一头接受30毫克/千克静脉注射的小母牛在注射后10小时内开始出现严重呼吸窘迫，并在注射后的第三天死亡。存在广泛的胸腔积液，并伴有其他肺部疾病的迹象。另一只接受40毫克/千克口服的动物未受影响。/白苏酮/

INJECTIONS OF 3 & 9 MG/KG, RESPECTIVELY, OF PERILLA KETONE DIRECTLY INTO THE RUMEN ELICITED NO RESPONSE IN ANGUS HEIFERS. ANOTHER HEIFER RECEIVING 30 MG/KG IV, HOWEVER, DEVELOPED SEVERE RESPIRATORY DISTRESS BEGINING WITHIN 10 HR & DIED ON THE THIRD DAY AFTER INJECTION. EXTENSIVE PLEURAL EFFUSION WAS PRESENT TOGETHER WITH OTHER PULMONARY DISEASE SIGNS. ANOTHER ANIMAL RECEIVING 40 MG/KG PER OS WAS UNAFFECTED. /PERILLA KETONE/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

一只成年公羊静脉注射了19毫克/千克的薄荷酮，在第3天出现了呼吸困难，但在注射后的第五天有所改善，当时它被宰杀。作为毒素的主要靶器官的肺，显示了局灶性毛细血管充血和肺泡内水肿。两只母山羊分别静脉注射了18毫克/千克和40毫克/千克，分别在12小时内因严重肺水肿死亡。10毫克/千克的剂量静脉注射导致另一只母山羊在36小时内死亡。将150毫克/千克的剂量注射到一只山羊的瘤胃中，导致受体在48小时内死亡。/薄荷酮/

AN ADULT MALE SHEEP RECEIVING 19 MG/KG OF PERILLA KETONE IV DEVELOPED RESPIRATORY DISTRESS ON DAY 3 BUT HAD IMPROVED SOMEWHAT BY THE FIFTH DAY POSTINJECTION, WHEN IT WAS SACRIFICED. THE LUNGS, AS PRIMARY TARGETS OF THE TOXIN, SHOWED FOCAL CAPILLARY CONGESTION & INTRAALVEOLAR EDEMA. TWO FEMALE GOATS INJECTED IV WITH 18 & 40 MG/KG, RESPECTIVELY, DIED WITHIN 12 HR WITH SEVERE PULMONARY EDEMA. A DOSE OF 10 MG/KG, IV KILLED ANOTHER FEMALE GOAT IN 36 HR. A DOSE OF 150 MG/KG INJECTED INTO THE RUMEN OF A GOAT RESULTED IN DEATH OF THE RECIPIENT IN 48 HR. /PERILLA KETONE/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

小马静脉注射18毫克/千克的紫苏酮后，在给药后几小时开始出现严重呼吸道疾病，病情逐渐加重，大约6小时后死亡。肺部病变的组织学特征与牛和山羊的急性牛肺水肿（ABPE）相似。相比之下，相当剂量的4-异丙醇产生的疾病要温和得多，这表明这个物种与牛不同，对紫苏酮的敏感性高于甘薯毒素。/紫苏酮/

PONIES INJECTED IV WITH 18 MG OF PERILLA KETONE/KG DEVELOPED A SEVERE RESPIRATORY DISEASE BEGINNING A FEW HR AFTER DOSING WHICH BECAME PROGRESSIVELY MORE SEVERE & ENDED IN DEATH ABOUT 6 HR LATER. THE LUNG LESIONS HISTOLOGICALLY WERE SIMILAR TO THOSE OF ACUTE BOVINE PULMONARY EDEMA (ABPE) IN CATTLE & GOATS. COMPARABLE DOSES OF 4-IPOMEANOL PRODUCED A MUCH MILDER DISEASE, SUGGESTING THAT THIS SPECIES, UNLIKE THE BOVINE, IS MORE SUSCEPTIBLE TO PERILLA KETONE THAN TO THE SWEET POTATO TOXIN. /PERILLA KETONE/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

野生的紫苏薄荷是俄克拉荷马州季节性大规模爆发的急性牛肺气肿（ABPE）综合症的另一个原因。对几个其他州类似爆发的回顾...表明这种爆发并不少见，尤其是在正常牧草可能稀缺的夏末或秋季发生。/最近/...田纳西州在夏末干旱后报告了爆发。将紫苏归咎为ABPE的原因是在动物的前胃或粪便中发现了紫苏种子的残余物，并在尸检时打开消化道时注意到了典型的紫苏薄荷气味。通常，除非牛因牧场草料短缺而饥饿，否则牛会避免吃紫苏。/Perilla frutescens/

FIELD INVESTIGATIONS.../PROVIDE/ STRONG EVIDENCE THAT WILD PERILLA MINT WAS ANOTHER CAUSE OF EXTENSIVE SEASONAL OUTBREAKS OF THE SYNDROME ACUTE BOVINE PULMONARY EMPHYSEMA (ABPE) IN OKLAHOMA. A REVIEW OF SIMILAR OUTBREAKS IN SEVERAL OTHER STATES...SUGGESTS THAT SUCH OUTBREAKS ARE NOT UNCOMMON, OCCURRING ESPECIALLY IN THE LATE SUMMER OR FALL WHEN NORMAL FORAGE MAY BE SCARCE. /RECENTLY/...OUTBREAKS HAVE BEEN REPORTED IN TENNESSEE FOLLOWING LATE SUMMER DROUGHT. INCRIMINATION OF PERILLA AS A CAUSATIVE AGENT OF ABPE WAS THE RESULT OF FINDING REMNANTS OF PERILLA SEEDS IN THE FORESTOMACHS OR DROPPINGS OF ANIMALS, & NOTING THE TYPICAL PERILLA MINT ODOR UPON OPENING THE GI TRACT AT AUTOPSY. GENERALLY, CATTLE WILL AVOID GRAZING PERILLA UNLESS DRIVEN BY HUNGER WHEN PASTURES ARE LOW. /PERILLA FRUTESCENS/

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为产物：
  描述：

  1-呋喃-3-基-4-甲基-戊-3-烯-1-醇 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到白苏烯酮
  参考文献：
  名称：

  Regioselectivity in electrochemical allylation of carbonyl compounds. A synthesis of egomaketone by regioselective allylation

  摘要：

  DOI：

  10.1021/jo00284a040

文献信息

• Palladium-catalyzed cross coupling of allyl halides with organotin reagents: a method of joining highly functionalized partners regioselectively and stereospecifically
  作者：Forrest K. Sheffy、J. P. Godschalx、J. K. Stille

  DOI：10.1021/ja00329a032

  日期：1984.8

  La reaction catalysee par le palladium d'halogenures allyliques avec des reactifs aryl- et vinylstannanes donne des produits de copulation croisee. En presence de monoxyde de carbone, des cetones sont obtenues, resultant d'une copulation croisee accompagnee d'une insertion de CO. La reaction est douce et s'effectue meme en presence de diverses fonctions (OH, OR, CN, CO 2 R, CHO) soit sur le chlorure

  La 反应催化剂 par le palladium d'halogenures allyliques avec des reactifs aryl- etvinylstannanes donne des produits de copulation croisee。En存在 de monooxyde de carbone, des cetones sont obtenues, result d'une copulation croisee accompagnee d'une insert de CO. La反应 est douce et s'effectue meme en 存在 de differents fonctions (OH, OR, CN, CO 2 R , CHO) soit sur le le chlorure allylique soit sur le stannane
• Regiospecific synthesis of 3,4-disubstituted furans and 3-substituted furans using 3,4-Bis(tri-n-butylstannyl)furan and 3-(tri-n-butylstannyl)f
  作者：Yun Yang、Henry N.C. Wong

  DOI：10.1016/s0040-4020(01)85528-9

  日期：1994.1

  3,4-Bis(tri-n-butylstannyl)furan and 3-(tri-n-butylstannyl)furan have been prepared and used successfully as building blocks to lead to various

  制备了3,4-双（三-正丁基锡烷基）呋喃和3-（三-正丁基锡烷基）呋喃，并成功地用作制造各种产品的基础。
• A new synthetic method for .BETA.,.GAMMA.-unsaturated ketones and a total synthesis of egomaketone.
  作者：Yasuo Ohtsuka、Toshimichi Sasahara、Takeshi Oishi

  DOI：10.1248/cpb.30.1106

  日期：——

  A new method for preparing β, γ-unsaturated ketones based on the intramolecular acyl N to C transfer of 2-carboxamidephenylsulfides is described including a total synthesis of egomaketone using this method.

  介绍了一种基于 2-脒基苯硫化物分子内酰基 N 到 C 的转移来制备 β、γ-不饱和酮的新方法，包括用这种方法全合成 egomaketone。
• TOKUDA, MASAO;SATOH, SHOHEI;SUGINOME, HIROSHI, J. ORG. CHEM., 54,(1989) N3, C. 5608-5613
  作者：TOKUDA, MASAO、SATOH, SHOHEI、SUGINOME, HIROSHI

  DOI：——

  日期：——